CN116583161A - Light emitting device and electronic apparatus including the same - Google Patents
Light emitting device and electronic apparatus including the same Download PDFInfo
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Abstract
Embodiments provide hairAn optical device and an electronic apparatus including the same. The light emitting device includes: a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, a first compound represented by formula 1, a second compound represented by formula 2, and at least one of a third compound represented by formula 3 and a fourth compound represented by formula 4, wherein the first compound to the fourth compound are different from each other, and the formulas 1 to 4 are described in the specification: [ 1 ]]
Description
Cross Reference to Related Applications
The present application claims priority and rights of korean patent application nos. 10-2022-0016967 and 10-2022-0063592, filed in the korean intellectual property office on day 2, 9, 2022 and day 5, 2022, 24, respectively, the entire contents of which are incorporated herein by reference.
Technical Field
The present disclosure relates to a light emitting device and an electronic apparatus including the same.
Background
Compared with the related art device, the light emitting device is a self-emission device, which has a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed, and generates a multicolor image.
In the light emitting device, a first electrode is disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes supplied from the first electrode move toward the emission layer through the hole transport region, and electrons supplied from the second electrode move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emissive layer to generate excitons. The excitons may transition from an excited state to a ground state, thereby generating light.
It will be appreciated that this background section is intended to provide a useful background for understanding the technology. However, this background section may also include ideas, concepts or cognizances that are not part of the knowledge or understanding of those skilled in the art prior to the corresponding effective application date of the subject matter disclosed herein.
Disclosure of Invention
Embodiments include a light emitting device having a low driving voltage, high efficiency, and long life, and an electronic apparatus including the light emitting device.
Additional aspects will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the embodiments of the disclosure.
According to an embodiment, a light emitting device may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and comprising an emissive layer; a first compound represented by formula 1; a second compound represented by formula 2; and at least one of a third compound represented by formula 3 and a fourth compound represented by formula 4, wherein the first to fourth compounds may be different from each other:
[ 1]
[ 2]
[ 3]
[ 4]
In the formulae 1 to 4,
L 11 to L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Can each independently be a single bond, unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
n11 to n14, n21 to n23, n31, n32, n41 and n42 may each independently be an integer selected from 1 to 3,
Ar 11 to Ar 14 、Ar 21 And Ar is a group 22 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
R 21 and R is 22 Can each independently be unsubstituted or deuterated, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 1 -C 30 Alkyl or C 3 -C 30 A cycloalkyl group,
R 31 and R is 32 Can each independently be unsubstituted or deuterium, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 3 -C 30 A cycloalkyl group,
CY 1 can be a phenyl group or a naphthyl group,
CY 41 and CY 42 Can each independently be C 5 -C 30 A carbocyclyl group, a carbonyl group,
T 3 and T 4 Each independently may be a group represented by formula 5,
[ 5]
Wherein, in the formula 5,
t may be C (X) 1 )(X 2 ) O, S or N (X) 1 )，
X 1 And X 2 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 30 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 5 -C 30 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 30 A heterocyclic group,
X 1 and X 2 Can optionally be linked to each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 30 A heterocyclic group,
wherein, in the formulas 1 to 5,
R 11 、R 23 、R 41 、R 42 and RT may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
a11 may be an integer selected from 0 to 6,
a23 may be an integer selected from 0 to 7,
a31 and a32 may each independently be an integer selected from 1 to 5,
a41 and a42 may each independently be an integer selected from 0 to 9,
at may be an integer selected from 0 to 7,
* Indicating the binding site to the adjacent atom,
R 10a the method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl compoundsRadical, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) And (2) and
Q 1 to Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently can be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
In an embodiment, the first electrode may be an anode; the second electrode may be a cathode; the interlayer may further include a hole transport region between the emission layer and the first electrode, and an electron transport region between the emission layer and the second electrode; the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof; and the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
In an embodiment, the hole transport region may include at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; at least one of the hole injection layer, the hole transport layer, and the electron blocking layer may include at least one of a first compound, a second compound, and a third compound and a fourth compound.
In an embodiment, the hole transport region may include a hole transport layer; the hole transport layer may include a first hole transport layer, a second hole transport layer, and a third hole transport layer; the first hole transport layer may be between the first electrode and the second hole transport layer; the first hole transport layer may include a first compound; the second hole transport layer may be between the first hole transport layer and the third hole transport layer; the second hole transport layer may include a second compound; and the third hole transport layer may include at least one of a third compound and a fourth compound.
In an embodiment, the hole transport region may include a hole transport layer; the hole transport layer may include a first hole transport layer, a second hole transport layer, a third hole transport layer, and a fourth hole transport layer; the first hole transport layer may be between the first electrode and the second hole transport layer; the first hole transport layer may include a first compound; the second hole transport layer may be between the first hole transport layer and the third hole transport layer; the second hole transport layer may include a second compound; the third hole transport layer may be between the second hole transport layer and the fourth hole transport layer; the third hole transport layer may include a third compound, and the fourth hole transport layer may include a fourth compound.
In embodiments, in formulas 1 to 4, L 11 To L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Each independently can be: a single bond; or each being unsubstituted or substituted by at least one R 10a Substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoboronpentadienyl, benzophospholpentadienyl, indenyl, benzothiophenyl, benzogermanium cyclopentenyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborolane, dibenzophosphorus cyclopentenyl,Fluorenyl, dibenzosilol, dibenzogermyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophen-5-oxide, 9H-fluoren-9-one, dibenzothiophen-5, 5-dioxide, azaindolyl, azabenzoborolidinyl, azabenzophospholanenyl, azaindenyl, azafused-on-5-oxide, azabenzoborolidinyl, azafused-on-9-one, azafused-on azabenzothiophene, azabenzogermanium heterocyclopenadienyl, azabenzothiophene, azabenzoselenophene, azabenzofuranyl, azacarbazolyl, azadibenzoborol, azadibenzophospholanyl, azafluorenyl, azadibenzosilol, azadibenzogermanium heterocyclopenadienyl, azacarbazolyl, azaborol, azacarbazolyl, azaborol, azadiphenyl, and azadiphenyl, aza, and aza Azadibenzothiophenyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophen-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophen-5, 5-dioxide, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolyl or 5,6,7, 8-tetrahydroquinolinyl, and R is 10a As defined in formulas 1 to 4.
In embodiments, in formulas 1 to 4, L 11 To L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Each independently may be a single bond or phenylene.
In embodiments, in formulas 1 and 2, ar 11 To Ar 14 、Ar 21 And Ar is a group 22 Each independently can be: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, triphenyleneA group selected from the group consisting of pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzil, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, and combinations thereof dibenzofuranyl, dibenzothienyl, dibenzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilolyl, dinaphthozolyl, cinnolyl, and cinnolyl indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothiophenocarbazolyl, benzothiopyrrolocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azadibenzosilol groups: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienylBenzosilol, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzofluorenyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzoxazolyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphtalofuranyl, dinaphtalothiophenyl, dinaphtalosilol, indenocarzolyl, indolocarbazolyl, benzocarbazolyl, benzothiophenocarzolyl, benzothiocarbazolyl, imidazopyrrolocarzolyl, imidazopyridinyl, imidazopyrimidinyl, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or any combination thereof, and
Q 31 to Q 33 Each independently can be: CH (CH) 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or each unsubstituted or deuterium-substituted, C 1 -C 20 An alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof, substituted with n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl.
In embodiments, in formulas 1 and 2, ar 11 To Ar 14 、Ar 21 And Ar is a group 22 Each independently can be: each unsubstituted or deuterium, -F, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Phenyl, naphthyl, phenanthryl, anthracyl, dibenzothiophene substituted with alkoxy, phenyl, or any combination thereofA radical or dibenzofuranyl radical.
In an embodiment, in formula 2, R 21 And R is 22 May be identical to each other.
In an embodiment, in formula 3, R 31 And R is 32 Can each independently be unsubstituted or deuterated, -F, cyano, C 1 -C 10 Alkyl or any combination thereof substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1]Heptyl, bicyclo [1.1.1]Amyl, bicyclo [2.1.1 ]]Hexyl or bicyclo [2.2.2 ]Octyl.
In an embodiment, in formula 4, CY 41 And CY 42 Each may be naphthyl; or CY 41 And CY 42 One of them may be naphthyl, and CY 41 And CY 42 The other of (2) may be phenyl or phenanthryl.
In embodiments, in formulas 1, 2 and 4, R 11 Can be hydrogen, deuterium or-F, and
R 23 、R 41 and R is 42 Each independently can be: hydrogen, deuterium or-F; or unsubstituted or deuterium, -F, cyano, C 1 -C 20 Alkyl groups or any combination thereof.
In an embodiment, in formula 5, X 1 And X 2 Each independently can be: c unsubstituted or substituted with deuterium, -F, cyano or any combination thereof 1 -C 10 An alkyl group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 2 -C 10 Alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1]Heptyl, bicyclo [1.1.1]Amyl, bicyclo [2.1.1 ]]Hexyl, bicyclo [2.2.2]Octyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl.
In an embodiment, in formula 5, when T is C (X 1 )(X 2 ) When X is 1 And X 2 May be identical to each other.
In an embodiment, in formula 5, RT may be: hydrogen, deuterium, -F, or cyano; or not (or)Substituted or by deuterium, -F, cyano, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy or any combination thereof 6 -C 10 Aryl groups.
In an embodiment, the emission layer may emit blue light having a maximum emission wavelength in a range of about 430nm to about 490 nm.
According to an embodiment, an electronic device may include a light emitting device.
In an embodiment, the electronic device may further include a thin film transistor, wherein the thin film transistor may include a source electrode and a drain electrode, and the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode.
In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
It will be understood that the above embodiments are described in a generic and descriptive sense only and not for purposes of limitation, and that the disclosure is not limited to the above embodiments.
Drawings
The above and other aspects and features of the present disclosure will become more apparent by describing in detail embodiments thereof with reference to the attached drawings in which:
fig. 1 is a schematic cross-sectional view of a light emitting device according to an embodiment;
FIG. 2 is a schematic cross-sectional view of an electronic device according to an embodiment; and is also provided with
Fig. 3 is a schematic cross-sectional view of an electronic device according to another embodiment.
Detailed Description
The present disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
In the drawings, the size, thickness, proportions and dimensions of elements may be exaggerated for ease of description and for clarity. Like numbers refer to like elements throughout.
In the description, it will be understood that when an element (or region, layer, section, etc.) is referred to as being "on," "connected to" or "coupled to" another element (or region, layer, section, etc.), it can be directly on, connected to or coupled to the other element (or region, layer, section, etc.), or one or more intervening elements (or regions, layers, sections, etc.) may be present therebetween. In a similar sense, when an element (or region, layer, section, etc.) is referred to as "overlying" another element (or region, layer, section, etc.), it can directly overlie the other element (or region, layer, section, etc.), or one or more intervening elements (or regions, layers, sections, etc.) may be present therebetween.
In the description, when an element (or region, layer, section, etc.) is "directly on," "directly connected to" or "directly coupled to" another element (or region, layer, section, etc.), there are no intervening elements (or regions, layers, sections, etc.). For example, "directly on" … … can mean that two layers or elements (or regions, portions, etc.) are provided without additional elements (or regions, layers, portions, etc.) such as adhesive elements therebetween.
As used herein, the use of expressions in the singular form, such as "a", "an", and "the" are intended to include the plural form as well, unless the context clearly indicates otherwise.
As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. For example, "a and/or B" may be understood to mean "A, B or a and B". The terms "and" or "may be used in a connective or compartmental sense and are to be understood as being equivalent to" and/or ".
In the specification and claims, for the purposes of their meaning and explanation, at least one of the terms "… …" is intended to include a meaning of "at least one selected from the group consisting of … …". For example, "at least one of A, B and C" may be understood to mean "a only, B only, C only, or any combination of two or more of A, B and C, such as ABC, ACC, BC or CC". The term "at least one of … …" modifies the entire list of elements when before/after the list of elements, rather than modifying individual elements of the list.
It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element may be termed a first element without departing from the scope of the present disclosure.
For ease of description, spatially relative terms "below," "under," "lower," "above," or "upper" and the like may be used herein to describe one element or component's relationship to another element or component as illustrated in the figures. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, where a device illustrated in the figures is turned over, elements located "below" or "beneath" another device could be oriented "above" the other device. Accordingly, the illustrative term "below" may include both a lower position and an upper position. The device may also be oriented in other directions, and therefore spatially relative terms may be construed differently depending on the orientation.
The term "about" or "approximately" as used herein includes the recited values and means that the measurement in question and the errors associated with the recited number of measurements (i.e., limitations of the measurement system) are considered within the acceptable deviation of the recited values as determined by one of ordinary skill in the art. For example, "about" may mean within one or more standard deviations of the recited values, or within ±20%, ±10% or ±5% of the recited values.
It will be understood that the terms "comprises," "comprising," "includes," "including," "having," "includes," "including," "containing," "includes," "including," "containing," "including," "having," "containing," "including," etc. are intended to specify the presence of stated features, integers, steps, operations, elements, components, or any combination thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or groups thereof.
The term "interlayer" as used herein may refer to a single layer and/or multiple layers between a first electrode and a second electrode of a light emitting device.
Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
One aspect provides a light emitting device, which may include:
a first electrode;
a second electrode facing the first electrode;
an interlayer between the first electrode and the second electrode and comprising an emissive layer;
a first compound represented by formula 1;
a second compound represented by formula 2; and
at least one of the third compound represented by formula 3 and the fourth compound represented by formula 4,
wherein the first to fourth compounds may be different from each other.
Hereinafter, the first compound, the second compound, the third compound, and the fourth compound will be described:
[ 1]
[ 2]
[ 3]
[ 4]
In the formulae 1 to 4,
L 11 to L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Can each independently be a single bond, unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl group, an
n11 to n14, n21 to n23, n31, n32, n41, and n42 may each independently be an integer selected from 1 to 3.
In embodiments, in formulas 1 to 4, L 11 To L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Each independently can be:
a single bond; or alternatively
Each unsubstituted or substituted by at least one R 10a Substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoboronpentadienyl, benzophosphole, indenyl, benzothiophenyl, benzogermanopyranyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoboronpentadienyl, dibenzophosphole, fluorenyl, dibenzosilol, dibenzogermane heterocycle Pentadienyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5, 5-dioxide, azaindolyl, azabenzoborolan, azabenzophospholanyl, azaindenyl, azabenzothiophenyl, azabenzosilol, azabenzofuranyl, azaborol, azabenzofuranyl, azabenzopencilyl, azabenzofuranyl, azabenzopencilyl, azathiophenyl, and azathiophenyl azabenzogermanium heterocyclopenadienyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborol, azadibenzophosphole, azafluorenyl, azadibenzosilol, azadibenzogermanium heterocyclopenadienyl, azadibenzothiophenyl, azaborol, azabenzofuranyl, azafuranyl, and azafuranyl azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene-5, 5-dioxide, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolinyl or 5,6,7, 8-tetrahydroisoquinolinyl, and is also provided with
R 10a May be the same as defined herein.
In embodiments, in formulas 1 to 4, L 11 To L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Each independently may be a single bond or phenylene.
In an embodiment, L 31 And L 32 May each independently be a group represented by one of formulae 2-1 to 2-3, and each of the formulae 2-1 to 2-3 indicates a binding site to an adjacent atom:
in embodiments, in formulas 1 to 4, n11 to n14, n21 to n23, n31, n32, n41, and n42 may each be independently 1 or 2.
In formula 1 and formula 2, ar 11 To Ar 14 、Ar 21 And Ar is a group 22 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group.
In embodiments, in formulas 1 and 2, ar 11 To Ar 14 、Ar 21 And Ar is a group 22 Each independently can be:
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, benzisoxazolyl, and the like tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, dibenzofluorenyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphtfuryl, dinaphthophioenyl, dinaphthophionyl, indenocarbazolyl, indolocarbazolyl, benzocarbazolyl, benzothiophenocarbazolyl, benzothiocarbazolyl, benzoxazolocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azadibenzothiarolyl). Deuterium, -F, -C l、-Br、-I、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzofluorenyl, benzocarbazolyl, naphtofuranyl, dinaphtalothienyl, dinaphtalosilol, indenocarbazolyl, indolocarbazolyl, benzocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or any combination thereof, and
Q 31 to Q 33 Each independently can be:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or alternatively
Each unsubstituted or deuterium-substituted, C 1 -C 20 An alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof, substituted with n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl.
In embodiments, in formulas 1 and 2, ar 11 To Ar 14 、Ar 21 And Ar is a group 22 Can each independently be unsubstituted or deuterated, -F, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl or any combination thereof.
In an embodiment, in formula 1, ar 11 To Ar 14 Can each independently be unsubstituted or deuterated, -F, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl or any combination thereof, and
in formula 2, ar 21 And Ar is a group 22 Can each independently be unsubstituted or deuterated, -F, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, or any combination thereof.
For example, in formula 1, ar 11 To Ar 14 Can each independently be phenyl or naphthyl, and in formula 2 Ar 21 And Ar is a group 22 Each independently may be phenyl, naphthyl or dibenzofuranyl.
In formula 2, R 21 And R is 22 Can each independently be unsubstituted or deuterated, -F, cyano, C 1 -C 10 Alkyl groupOr any combination thereof 1 -C 30 Alkyl or C 3 -C 30 Cycloalkyl groups.
The term "cycloalkyl" as used herein may refer not only to a monocyclic group, such as cyclohexyl, but also to a fused ring unsaturated hydrocarbon group, such as adamantyl.
In an embodiment, in formula 2, R 21 And R is 22 Can each independently be C each unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof 1 -C 10 Alkyl or C 3 -C 10 Cycloalkyl groups.
In an embodiment, in formula 2, R 21 And R is 22 Each independently can be:
methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl or tert-decyl each unsubstituted or substituted with deuterium, -F, cyano or any combination thereof; or (b)
Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1] heptyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl or bicyclo [2.2.2] octyl.
In an embodiment, in formula 2, R 21 And R is 22 May be identical to each other.
In formula 3, R 31 And R is 32 Can each independently be unsubstituted or deuterium, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 3 -C 30 Cycloalkyl groups. In formula 2, R 31 And R is 32 May be the same as or different from each other.
In an embodiment, in formula 3, R 31 And R is 32 Can each independently be unsubstituted or deuterated, -F, cyano, C 1 -C 10 Alkyl groupOr any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1]Heptyl, bicyclo [1.1.1]Amyl, bicyclo [2.1.1]]Hexyl or bicyclo [2.2.2]Octyl.
In an embodiment, in formula 3, R 31 And R is 32 Can each independently be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1]Heptyl or bicyclo [2.2.2]Octyl.
For example, in formula 3, R 31 Can be cyclohexyl, adamantyl or bicyclo [2.2.1]]Heptyl, and R 32 Can be bicyclo [2.2.1]]Heptyl, but embodiments are not limited thereto.
In formula 1, CY 1 Can be phenyl or naphthyl.
In an embodiment, in formula 1, CY 1 May be a group represented by one of formulas 1-1 to 1-4:
in formulas 1-1 to 1-4, a binding site to a nitrogen atom is indicated, and a binding site to a carbon atom is indicated.
In formula 4, CY 41 And CY 42 Can each independently be C 5 -C 30 Carbocyclyl.
In an embodiment, in formula 4, CY 41 And CY 42 Can each independently be C 6 -C 20 An aromatic hydrocarbon group.
For example, in formula 4, CY 41 And CY 42 And each independently may be phenyl, naphthyl, anthryl or phenanthryl.
In an embodiment, in formula 4, CY 41 And CY 42 And each independently may be phenyl, naphthyl or phenanthryl.
In an embodiment, in formula 4, CY 41 And CY 42 Each may be naphthyl; or CY 41 And CY 42 One of them may be naphthyl, and CY 41 And CY 42 The other of (2) may be phenyl or phenanthryl.
In formula 3 and formula 4, T 3 And T 4 Each independently may be a group represented by formula 5:
[ 5]
In the case of the method of claim 5,
t may be C (X) 1 )(X 2 ) O, S or N (X) 1 )，
X 1 And X 2 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 30 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 5 -C 30 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 30 Heterocyclyl, and
X 1 and X 2 Can optionally be linked to each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 30 A heterocyclic group.
In formula 5, the binding sites to adjacent atoms are indicated.
In the formulae 1 to 5,
R 11 、R 23 、R 41 、R 42 and RT may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
a11 may be an integer selected from 0 to 6,
a23 may be an integer selected from 0 to 7,
a31 and a32 may each independently be an integer selected from 1 to 5,
a41 and a42 may each independently be an integer selected from 0 to 9, and
at may be an integer selected from 0 to 7.
In embodiments, a11 indicates binding to CY 1 The number of substituents of (a) is defined. For example, when CY 1 When a is a group represented by formula 1-1, a11 may be an integer selected from 0 to 4, and when CY 1 When a is a group represented by one of formulas 1-2 to 1-4, a11 may be an integer selected from 0 to 6.
In an embodiment, a41 and a42, respectively, are indicative of binding to CY 41 And CY 42 The number of substituents of (a) is defined. For example, when CY 41 When phenyl, a41 may be an integer selected from 0 to 5, when CY 41 When naphthyl, a41 may be an integer selected from 0 to 7, and when CY 41 In the case of phenanthryl, a41 may be an integer selected from 0 to 9.
In embodiments, in formula 1, formula 2, and formula 4, a11, a23, a41, and a42 may each independently be 0, 1, or 2.
In an embodiment, in formula 3, a31 and a32 may each be independently 1 or 2. For example, a31 and a32 may each be 1.
In embodiments, in formula 1, formula 2, formula 4, and formula 5, R 11 、R 23 、R 41 、R 42 And RT may each independently be:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
each of which is deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzoxazolyl benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzofluorenyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzoxazolyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphtalofuranyl, dinaphtalothiophenyl, dinaphtalosilol, indenocarbazolyl, indolocarbazolyl, benzocarbazolyl, benzothiophenocarbazolyl, benzothiophenyl, benzothiopheno Carbazolyl, imidazopyridinyl, imidazopyrimidinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azadibenzosilol groups): deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzofluorenyl, benzocarbazolyl, naphtofuranyl, dinaphtalothienyl, dinaphtalosilol, indenocarbazolyl, indolocarbazolyl, benzocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or any combination thereof; or (b)
-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 ) And (2) and
Q 1 to Q 3 And Q 31 To Q 33 Each independently can be:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
Each unsubstituted or deuterium-substituted, C 1 -C 20 An alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof, substituted with n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl.
In embodiments, in formulas 1, 2 and 4,
R 11 can be hydrogen, deuterium or-F, and
R 23 、R 41 and R is 42 Each independently can be: hydrogen, deuterium or-F; or unsubstituted or deuterium, -F, cyano, C 1 -C 20 Alkyl groups or any combination thereof.
For example, R 11 May be hydrogen.
For example, R 23 May be hydrogen or phenyl, but the embodiment is not limited thereto.
For example, R 41 And R is 42 May each independently be hydrogen or phenyl.
For example, R 41 And R is 42 One of which may be hydrogen, and R 41 And R is 42 The other of (a) may be a phenyl group, but the embodiment is not limited thereto.
In practiceIn embodiments, T in formula 3 3 And T in formula 4 4 May be the same or different from each other.
With respect to formula 5, the expression "X" as used herein 1 And X 2 The linking to each other to form a cyclic group "may include:
wherein X is 1 And X 2 A case of being directly linked to each other to form a cyclic group; or (b)
Wherein X is 1 And X 2 By single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 5 In the case where alkenylenes are attached to each other to form a cyclic group.
For example, in compound 129, T may be C (X 1 )(X 2 ) Wherein X is 1 And X 2 Each may be phenyl and may be linked to each other via a single bond to form a fluorenyl group. However, the embodiments are not limited thereto, and may be implemented in various forms.
For example, in compound 143, T may be C (X 1 )(X 2 ) Wherein X is 1 And X 2 Each may be ethyl and may be linked to each other via a single bond to form a cyclopentyl group. However, the embodiments are not limited thereto, and may be implemented in various forms.
In an embodiment, in formula 5, X 1 And X 2 Each independently can be:
c unsubstituted or substituted with deuterium, -F, cyano or any combination thereof 1 -C 10 An alkyl group; or (b)
Each unsubstituted or deuterium, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 2 -C 10 Alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1 ]Heptyl, bicyclo [1.1.1]Amyl, bicyclo [2.1.1]]Hexyl, bicyclo [2.2.2]Octyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl.
For example, X 1 And X 2 Can each beIndependently is:
methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl or tert-decyl;
ethenyl, propenyl, butenyl, pentenyl or hexenyl;
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1] heptyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl or bicyclo [2.2.2] octyl; or (b)
Phenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl.
In an embodiment, in formula 5, when T is C (X 1 )(X 2 ) When X is 1 And X 2 May be identical to each other.
In an embodiment, in formula 5, RT may be:
Hydrogen, deuterium, -F, or cyano; or (b)
Unsubstituted or deuterium-F, cyano, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy or any combination thereof 6 -C 10 Aryl groups.
In an embodiment, in formula 5, RT may be:
hydrogen; or (b)
Phenyl unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof.
For example, in formula 5, RT may be hydrogen or phenyl.
In an embodiment, in formula 5, at may be 0 or 1.
In an embodiment, the group represented by formula 5 may be a group represented by one of formulas 5-1 to 5-5:
in the formulae 5-1 to 5-5,
RT 1 can be the same as defined in formula 5 for RT, except for RT 1 May not be hydrogen;
t may be the same as defined in formula 5; and is also provided with
* Indicating the binding sites to adjacent atoms.
In embodiments, R 10a The method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) And (2) and
Q 1 to Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently can be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
In an embodiment, the first compound may include at least one of compounds 1 to 93, the second compound may include at least one of compounds 94 to 123, the third compound may include at least one of compounds 124 to 183, and the fourth compound may include at least one of compounds 184 to 207, but the embodiment is not limited thereto.
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The synthetic methods of the first to fourth compounds (hereinafter, referred to as "amine compounds" in some embodiments) may be identified by one of ordinary skill in the art by reference to the following synthetic examples and/or examples.
In an embodiment, the first compound; a second compound; and at least one of the third compound and the fourth compound may be included between the first electrode and the second electrode of the light emitting device. For example, a first compound; a second compound; and at least one of the third compound and the fourth compound may be included in an interlayer of the light emitting device.
In the present embodiment of the present invention,
the first electrode of the light emitting device may be an anode,
the second electrode of the light emitting device may be a cathode,
the interlayer may further comprise a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode,
the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
In an embodiment, the hole transport region may include: a first compound; a second compound; and at least one of a third compound and a fourth compound.
In an embodiment, the hole transport region may include at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and
at least one of the hole injection layer, the hole transport layer, and the electron blocking layer may include: a first compound; a second compound; and at least one of a third compound and a fourth compound.
In an embodiment, the hole transport region may include a hole transport layer, and the hole transport layer may include: a first compound; a second compound; and at least one of a third compound and a fourth compound.
In an embodiment, the hole transport region may include a hole injection layer and a hole transport layer, and the hole transport layer may include: a first compound; a second compound; and at least one of a third compound and a fourth compound.
When the hole transport layer has a multi-layer structure, the driving voltage and light emission efficiency of the light emitting device may be significantly affected by the compound included in the hole transport layer disposed close to the emission layer, and the lifetime characteristics of the light emitting device may be relatively significantly affected by the compound included in the hole transport layer disposed away from the emission layer.
The third compound includes a cycloalkane group having high rigidity (R in formula 3 31 And R is 32 ) And thus may have excellent optical properties. In addition to T 4 (which is a group represented by formula 5), the fourth compound further includes a carbocyclyl group such as CY 41 And CY 42 Due to the high planarity of the entire molecule, it is possible to have excellent charge transport properties and, in this respect, excellent stability during charge transport. Therefore, when at least one of the third compound and the fourth compound is included in the hole transport layer disposed near the emission layer, the driving voltage and the light emitting efficiency of the light emitting device can be significantly improved.
In embodiments, the hole transport region may include a hole transport layer,
the hole transport layer may include a first hole transport layer, a second hole transport layer and a third hole transport layer,
the first hole transport layer may be between the first electrode and the second hole transport layer,
the first hole transport layer may comprise a first compound,
the second hole transport layer may be between the first hole transport layer and the third hole transport layer,
the second hole transport layer may include a second compound, and
the third hole transport layer may include at least one of a third compound and a fourth compound.
In the above embodiments, the first hole transport layer, the second hole transport layer, and the third hole transport layer may be in direct contact with each other, or other organic layers and/or inorganic layers may be disposed between the first hole transport layer and the second hole transport layer, and/or between the second hole transport layer and the third hole transport layer.
In an embodiment, the first hole transport layer, the second hole transport layer, and the third hole transport layer may be in direct contact with each other. For example, the second hole transport layer may directly contact each of the first hole transport layer and the third hole transport layer.
When at least one of the third compound and the fourth compound is included in the third hole transporting layer disposed near the emission layer, the driving voltage and the light emitting efficiency of the light emitting device can be significantly improved.
For example, the third hole transport layer may include only the third compound.
For example, the third hole transport layer may include both a third compound and a fourth compound.
In embodiments, the hole transport region may include a hole transport layer,
the hole transport layer may include a first hole transport layer, a second hole transport layer, a third hole transport layer and a fourth hole transport layer,
the first hole transport layer may be between the first electrode and the second hole transport layer,
the first hole transport layer may comprise a first compound,
the second hole transport layer may be between the first hole transport layer and the third hole transport layer,
the second hole transport layer may comprise a second compound,
the third hole transport layer may be between the second hole transport layer and the fourth hole transport layer,
The third hole transport layer may include a third compound, and
the fourth hole transport layer may include a fourth compound.
In the above embodiments, the first hole transport layer, the second hole transport layer, the third hole transport layer, and the fourth hole transport layer may be in direct contact with each other, or other organic and/or inorganic layers may be disposed between the first hole transport layer and the second hole transport layer, and/or between the second hole transport layer and the third hole transport layer, and/or between the third hole transport layer and the fourth hole transport layer.
In an embodiment, the first hole transport layer, the second hole transport layer, the third hole transport layer, and the fourth hole transport layer may be in direct contact with each other. For example, the second hole transport layer may directly contact each of the first hole transport layer and the third hole transport layer, and the third hole transport layer may directly contact each of the second hole transport layer and the fourth hole transport layer.
When the third compound and the fourth compound are included in the third hole transport layer and the fourth hole transport layer, respectively, which are disposed near the emission layer, the driving voltage and the light emitting efficiency of the light emitting device can be significantly improved.
In an embodiment, an emission layer of an interlayer in a light emitting device may include a dopant and a host. For example, the host may include an anthracene compound, but is not limited thereto, and the dopant may include a dopant containing C 8 -C 60 A compound of polycyclic groups in which at least two cyclic groups are fused while sharing boron (B). However, the embodiment is not limited thereto.
The amount of host may be greater than the amount of dopant. For example, the amount of dopant in the emissive layer may be in the range of about 0.01 parts by weight to about 5 parts by weight based on 100 parts by weight total of host and dopant. For example, the amount of dopant in the emissive layer may be in the range of about 0.01 parts by weight to about 3 parts by weight based on 100 parts by weight total of host and dopant. However, the embodiment is not limited thereto.
The emission layer may emit red, green, blue, and/or white light. For example, the emissive layer may emit blue light. Blue light may have a maximum emission wavelength, for example, in the range of about 400nm to about 490 nm. For example, in an embodiment, the emissive layer may emit blue light having a maximum emission wavelength in the range of about 430nm to about 490 nm.
In an embodiment, the light emitting device may include a capping layer outside the first electrode or outside the second electrode.
For example, the light emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode, and at least one of the first capping layer and the second capping layer may include at least one of a first compound to a fourth compound. The first capping layer and/or the second capping layer may each be the same as described herein.
In an embodiment, the light emitting device may further include:
a first capping layer outside the first electrode, and the first capping layer includes at least one of a first compound to a fourth compound;
a second capping layer outside the second electrode, and the second capping layer includes at least one of the first to fourth compounds; or (b)
Both the first capping layer and the second capping layer.
The phrase "(interlayer and/or capping layer) as used herein includes a case where" the first compound represented by formula 1 "means" (interlayer and/or capping layer) may include one kind of "the first compound represented by formula 1" or a case where "(interlayer and/or capping layer) may include two or more different kinds of" the first compound represented by formula 1 ". The second compound to the fourth compound may each be explained in the same manner.
For example, the interlayer and/or the capping layer may include only compound 1 as an amine compound. Thus, the compound 1 may be included in a hole transport region of the light emitting device. For example, the interlayer may include both compound 1 and compound 2 as amine compounds. Compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the hole transport region), or may be present in different layers (e.g., compound 1 may be present in the emissive layer, and compound 2 may be present in the hole transport region).
Another aspect provides an electronic device that may include a light emitting apparatus. The electronic device may further include a thin film transistor.
For example, in an embodiment, the electronic device may further include a thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. The electronic device may be the same as described herein.
The first compound to the fourth compound are each an amine compound and have a condensed ring structure in the molecule (see fluorenyl group and the like in formula 1; carbazolyl group and fluorenyl group and the like in formula 2; T in formula 3) 3 Etc.; t in formula 4 4 Etc.), the first to fourth compounds may have a high glass transition temperature (Tg) and/or a high melting point so that crystallization may be prevented. Among the first to fourth compounds, heat resistance to heat generated during light emission and high temperature resistance under a high temperature environment can be increased, resulting in excellent electrical stability and excellent charge transport ability.
Because the third compound includes cycloalkyl groups having high rigidity (R in formula 3 31 And R is 32 ) The third compound may have excellent optical properties. Since the fourth compound has high flatness of the entire molecule, the fourth compound may have excellent charge transporting property, and thus is also highly stable during charge transport.
Therefore, when the first to third compounds or the first to fourth compounds are used as a hole transporting material, an electronic device (e.g., an organic light emitting device) having characteristics of low driving voltage, high luminance, high light emitting efficiency, and long lifetime can be realized.
[ description of FIG. 1 ]
Fig. 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.
The structure of the light emitting device 10 and the method of manufacturing the light emitting device 10 according to the embodiment will be described below with reference to fig. 1.
[ first electrode 110]
In fig. 1, the substrate may further include under the first electrode 110 or over the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In embodiments, the substrate may be a flexible substrate, for example, may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate (PET), polyaromatic ester (PAR), polyetherimide, or any combination thereof.
For example, the first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material used to form the first electrode 110 may be a high work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 may include indium tin oxide (ITO, indium Zinc Oxide (IZO), tin oxide (SnO) 2 ) Zinc oxide (ZnO) or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The first electrode 110 may have a structure composed of a single layer or a structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
Interlayer 130
The interlayer 130 is disposed on the first electrode 110. The interlayer 130 may include an emissive layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
In an embodiment, the interlayer 130 may further include a metal-containing compound (such as an organometallic compound), an inorganic material (such as quantum dots), and the like, in addition to various organic materials.
The interlayer 130 may include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between the two or more emission units. When the interlayer 130 includes two or more emission units and at least one charge generation layer, the light emitting device 10 may be a tandem light emitting device.
[ hole transport region in interlayer 130 ]
The hole transport region may have: a structure consisting of layers (consisting of a single material); a structure composed of layers including a plurality of materials different from each other; or a structure including a plurality of layers including a plurality of materials different from each other.
The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
In an embodiment mode, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein layers of each structure may be stacked in their respective stated order from the first electrode 110, but the structure of the hole transport region is not limited thereto.
The hole transport region may include: a first compound; a second compound; and at least one of a third compound and a fourth compound.
The hole transporting region may further include, in addition to the first to fourth compounds: a compound represented by formula 201, a compound represented by formula 202, or any combination thereof:
[ 201]
[ 202]
In the formulas 201 and 202 of the present embodiment,
L 201 to L 204 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
L 205 can be-O ', -S', -N (Q) 201 ) Unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xa1 to xa4 may each independently be an integer selected from 0 to 5,
xa5 may be an integer selected from 1 to 10,
R 201 to R 204 And Q 201 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
R 201 and R is 202 Optionally via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 5 Alkenylene groups are bonded to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 8 -C 60 Polycyclic groups (e.g., carbazole)Radical, etc.) (e.g., compound HT16, etc.),
R 203 and R is 204 Optionally via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 5 Alkenylene groups are bonded to each other to form a group that is unsubstituted or substituted with at least one R 10a Substituted C 8 -C 60 A polycyclic group, and
na1 may be an integer selected from 1 to 4.
In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 may each independently include at least one of the groups represented by formulas CY201 to CY 217:
in formulae CY201 to CY217, R 10b And R is 10c Can each independently be R 10a Is the same as the description of Cy 201 To ring CY 204 Can each independently be C 3 -C 20 Carbocyclyl or C 1 -C 20 Heterocyclyl, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or R as described herein 10a And (3) substitution.
In an embodiment, in formulas CY201 through CY217, the ring CY 201 To ring CY 204 And each independently may be phenyl, naphthyl, phenanthryl or anthracyl.
In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 may each independently include at least one of the groups represented by formulas CY201 to CY 203.
In an embodiment, the compound represented by formula 201 may include at least one of the groups represented by formulas CY201 to CY203 and at least one of the groups represented by formulas CY204 to CY 217.
In an embodiment, xa1 may be 1, R in formula 201 201 Can be one of the groups represented by the formulae CY201 to CY203, xa2 may be 0, and R 202 May be one of the groups represented by formulas CY204 to CY 207.
In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 may each not include a group represented by formulas CY201 to CY 203.
In embodiments, the compound represented by formula 201 and the compound represented by formula 202 may each not include a group represented by formulas CY201 to CY203, and may each independently include at least one of groups represented by formulas CY204 to CY 217.
In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 may each not include a group represented by formulas CY201 to CY 217.
In embodiments, the hole transport region may include one of compounds HT1 through HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β -NPB, TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4',4 "-tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-styrenesulfonate) (PANI/PSS), or any combination thereof:
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The hole transport region may have a thickness of aboutTo about->Within a range of (2). For example, the thickness of the hole transport region may be about +.>To about->Within a range of (2). When the hole transport region comprises a hole injection layer, a hole transport layer, or any combination thereof, the hole injection layer may have a thickness of about +.>To about->Within a range of (2), and the thickness of the hole transport layer may be about +.>To about->Within a range of (2). For example, the thickness of the hole injection layer may be about +.> To about->Within a range of (2). For example, the thickness of the hole transport layer may be about +.>To about->Within a range of (2). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
The emission auxiliary layer may increase light emission efficiency by compensating an optical resonance distance according to a wavelength of light emitted from the emission layer, and the electron blocking layer may block electrons from leaking from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission assistance layer and the electron blocking layer.
[ p-dopant ]
In addition to these materials, the hole transport region may further include a charge generating material for improving the conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge generating material).
The charge generating material may be, for example, a p-dopant.
For example, the p-dopant may have a Lowest Unoccupied Molecular Orbital (LUMO) level equal to or less than about-3.5 eV.
In embodiments, the p-dopant may include quinone derivatives, cyano-containing compounds, compounds including element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ and F4-TCNQ, etc.
Examples of the cyano group-containing compound may include HAT-CN and a compound represented by formula 221, and the like:
[ 221]
In the process of 221,
R 221 to R 223 Can be each independentlyIs unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl group, and
R 221 to R 223 At least one of which may each independently be C substituted with 3 -C 60 Carbocyclyl or C 1 -C 60 A heterocyclic group: cyano group; -F; -Cl; -Br; -I; c substituted with cyano, -F, -Cl, -Br, -I, or any combination thereof 1 -C 20 An alkyl group; or any combination thereof.
In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.
Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.; post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.), etc.
Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
Examples of nonmetallic materials may include oxygen (O) and halogens (e.g., F, cl, br, I, etc.), and the like.
Examples of compounds including elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.
Examples of the metal oxide may include tungsten oxide (e.g., WO, W 2 O 3 、WO 2 、WO 3 、W 2 O 5 Etc.), vanadium oxides (e.g., VO, V 2 O 3 、VO 2 、V 2 O 5 Etc.), molybdenum oxide (MoO, mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 Etc.) and rhenium oxide (e.g., reO 3 Etc.), etc.
Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.
Examples of the alkali metal halide may include LiF, naF, KF, rbF, csF, liCl, naCl, KCl, rbCl, csCl, liBr, naBr, KBr, rbBr, csBr, liI, naI, KI, rbI and CsI, etc.
Examples of alkaline earth metal halides may include BeF 2 、MgF 2 、CaF 2 、SrF 2 、BaF 2 、BeCl 2 、MgCl 2 、CaCl 2 、SrCl 2 、BaCl 2 、BeBr 2 、MgBr 2 、CaBr 2 、SrBr 2 、BaBr 2 、BeI 2 、MgI 2 、CaI 2 、SrI 2 And BaI 2 Etc.
Examples of transition metal halides may include titanium halides (e.g., tiF 4 、TiCl 4 、TiBr 4 、TiI 4 Etc.), zirconium halides (e.g., zrF 4 、ZrCl 4 、ZrBr 4 、ZrI 4 Etc.), hafnium halides (e.g., hfF 4 、HfCl 4 、HfBr 4 、HfI 4 Etc.), vanadium halides (e.g., VF 3 、VCl 3 、VBr 3 、VI 3 Etc.), niobium halides (e.g., nbF 3 、NbCl 3 、NbBr 3 、NbI 3 Etc.), tantalum halides (e.g., taF 3 、TaCl 3 、TaBr 3 、TaI 3 Etc.), chromium halides (e.g., crF 3 、CrCl 3 、CrBr 3 、CrI 3 Etc.), molybdenum halides (e.g., moF 3 、MoCl 3 、MoBr 3 、MoI 3 Etc.), tungsten halides (e.g., WF 3 、WCl 3 、WBr 3 、WI 3 Etc.), manganese halides (e.g., mnF 2 、MnCl 2 、MnBr 2 、MnI 2 Etc.), technetium halides (e.g., tcF 2 、TcCl 2 、TcBr 2 、TcI 2 Etc.), rhenium halides (e.g., ref 2 、ReCl 2 、ReBr 2 、ReI 2 Etc.), ferrous halides (e.g., feF 2 、FeCl 2 、FeBr 2 、FeI 2 Etc.), ruthenium halides (e.g., ruF 2 、RuCl 2 、RuBr 2 、RuI 2 Etc.), osmium halides (e.g., osF 2 、OsCl 2 、OsBr 2 、OsI 2 Etc.), cobalt halides (e.g., coF 2 、CoCl 2 、CoBr 2 、CoI 2 Etc.), rhodium halides (e.g., rhF 2 、RhCl 2 、RhBr 2 、RhI 2 Etc.), iridium halides (e.g., irF 2 、IrCl 2 、IrBr 2 、IrI 2 Etc.), nickel halides (e.g., niF 2 、NiCl 2 、NiBr 2 、NiI 2 Etc.), palladium halides (e.g., pdF 2 、PdCl 2 、PdBr 2 、PdI 2 Etc.), platinum halides (e.g., ptF 2 、PtCl 2 、PtBr 2 、PtI 2 Etc.), cuprous halides (e.g., cuF, cuCl, cuBr, cuI, etc.), silver halides (e.g., agF, agCl, agBr, agI, etc.), and gold halides (e.g., auF, auCl, auBr, auI, etc.), etc.
Examples of late transition metal halides may include zinc halides (e.g., znF 2 ，ZnCl 2 ，ZnBr 2 ，ZnI 2 Etc.), indium halides (e.g., inI 3 Etc.) and tin halides (e.g., snI 2 Etc.), etc.
Examples of lanthanide metal halides may include YbF, ybF 2 、YbF 3 、SmF 3 、YbCl、YbCl 2 、YbCl 3 、SmCl 3 、YbBr、YbBr 2 、YbBr 3 、SmBr 3 、YbI、YbI 2 、YbI 3 And SmI 3 Etc.
Examples of metalloid halides may include antimony halides (e.g., sbCl 5 Etc.), etc.
Examples of the metal telluride may include alkali metal telluride (e.g., li 2 Te、Na 2 Te、K 2 Te、Rb 2 Te、Cs 2 Te, etc.), alkaline earth metal telluride (e.g., beTe, mgTe, caTe, srTe, baTe, etc.), transition metal telluride (e.g., tiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 、Nb 2 Te 3 、Ta 2 Te 3 、Cr 2 Te 3 、Mo 2 Te 3 、W 2 Te 3 、MnTe、TcTe、ReTe、FeTe、RuTe、OsTe、CoTe、RhTe、IrTe、NiTe、PdTe、PtTe、Cu 2 Te、CuTe、Ag 2 Te、AgTe、Au 2 Te, etc.), late transition metal telluride (e.g., znTe, etc.), and lanthanide metal telluride (e.g., laTe, ceTe, prTe, ndTe, pmTe, euTe, gdTe, tbTe, dyTe, hoTe, erTe, tmTe, ybTe, luTe, etc.), etc.
[ emissive layer in interlayer 130 ]
When the light emitting device 10 is a full color light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer according to the subpixels. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers may contact each other or may be separated from each other to emit white light. In an embodiment, the emission layer may include two or more materials among a red light emitting material, a green light emitting material, and a blue light emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
The emissive layer may include a host and a dopant. The dopant may include phosphorescent dopants, fluorescent dopants, or any combination thereof.
The amount of dopant in the emissive layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
In an embodiment, the emissive layer may include quantum dots.
In an embodiment, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or dopant in the emissive layer.
The thickness of the emissive layer may be aboutTo about->Within a range of (2). For example, the thickness of the emissive layer may be aboutTo about->Within a range of (2). When the thickness of the emission layer is within these ranges, excellent light emission characteristics can be obtained without significantly increasing the driving voltage.
[ Main body ]
In an embodiment, the host may include a compound represented by formula 301:
[ 301]
[Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 。
In the formula (301) of the present invention,
Ar 301 and L 301 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xb11 may be 1, 2 or 3,
xb1 may be an integer selected from 0 to 5,
R 301 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substitution ofC of (2) 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, -Si (Q) 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(＝O)(Q 301 )、-S(＝O) 2 (Q 301 ) or-P (=O) (Q 301 )(Q 302 )，
xb21 may be an integer selected from 1 to 5, and
Q 301 to Q 303 Can be each independently from reference Q 1 The description is the same.
For example, in formula 301, when xb11 is 2 or more, two or more Ar 301 Can be bonded to each other via a single bond.
In an embodiment, the host may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:
[ 301-1]
[ 301-2]
In the formulas 301-1 and 301-2,
ring A 301 To ring A 304 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
X 301 can be O, S, N [ (L) 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) Or Si (R) 304 )(R 305 )，
xb22 and xb23 may each independently be 0, 1 or 2,
L 301 xb1 and R 301 May each be the same as described herein,
L 302 to L 304 Can be each independently from reference L 301 The same is described with respect to the case,
xb2 to xb4 may each independently be the same as described with reference to xb1, and
R 302 To R 305 And R is 311 To R 314 Can be each independently from reference R 301 The description is the same.
In embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In embodiments, the host may include Be complexes (e.g., compound H55), mg complexes, zn complexes, or any combination thereof.
In embodiments, the host may include one of compounds H1 through H125, 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-methyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), 9, 10-bis (2-naphthyl) -2-tert-butyl-anthracene (TBADN), 4 '-bis (N-carbazolyl) -1,1' -biphenyl (CBP), 1, 3-bis (9-carbazolyl) benzene (mCP), 1,3, 5-tris (carbazol-9-yl) benzene (TCP), or any combination thereof:
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[ phosphorescent dopant ]
The phosphorescent dopant may include at least one transition metal as a central metal.
Phosphorescent dopants may include monodentate ligands, bidentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
Phosphorescent dopants may be electrically neutral.
In an embodiment, the phosphorescent dopant may include an organometallic compound represented by formula 401:
[ 401]
M(L 401 ) xc1 (L 402 ) xc2 ，
In the formula (401) of the present invention,
m may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
L 401 May be a ligand represented by formula 402, and xc1 may be 1, 2, or 3, wherein when xc1 is 2 or more, two or more L 401 May be the same as or different from each other,
[ 402]
L 402 May be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 May be the same as or different from each other,
in formula 402, X 401 And X 402 Each of which may independently be nitrogen or carbon,
ring A 401 And ring A 402 Can each independently be C 3 -C 60 Carbocyclyl or C 1 -C 60 A heterocyclic group,
T 401 can be single bond, —o ', -S', -C (=o) -, -N (Q) 411 )-*'、*-C(Q 411 )(Q 412 )-*'、
*-C(Q 411 )＝C(Q 412 )-*'、*-C(Q 411 ) Either = 'or = C =',
X 403 and X 404 Can each independently be a chemical bond (e.g., covalent or coordinate), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) Or Si (Q) 413 )(Q 414 )，
Q 411 To Q 414 Can be each independently from reference Q 1 The same is described with respect to the case,
R 401 and R is 402 Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, -Si (Q) 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(＝O)(Q 401 )、-S(＝O) 2 (Q 401 ) or-P (=O) (Q 401 )(Q 402 )，
Q 401 To Q 403 Can be independently of each otherGround and reference Q 1 The same is described with respect to the case,
xc11 and xc12 may each independently be an integer selected from 0 to 10, and
Each of the formulae 402 and 401 indicates a binding site to M in formula 401.
In an embodiment, in formula 402, X 401 Can be nitrogen, and X 402 Can be carbon, or X 401 And X 402 Each may be nitrogen.
In an embodiment, in formula 401, when xc1 is 2 or more, at two or more L 401 In two rings A 401 Optionally via T as a linking group 402 Are connected to each other and two rings A 402 Optionally also via T as a linking group 403 To each other (see, for example, compounds PD1 to PD4 and PD 7). T (T) 402 And T 403 Can be each independently from reference T 401 The description is the same.
In formula 401, L 402 May be an organic ligand. For example, L 402 May include halo, diketo (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), C (=o), isonitrile, -CN, phosphorus-containing (e.g., phosphine, phosphite, etc.), or any combination thereof.
Phosphorescent dopants may include, for example, one of compounds PD1 through PD39, or any combination thereof:
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[ fluorescent dopant ]
The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or any combination thereof.
In an embodiment, the fluorescent dopant may include a compound represented by formula 501:
[ 501]
In the formula (501) of the present invention,
Ar 501 、L 501 to L 503 、R 501 And R is 502 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xd1 to xd3 can each independently be 0, 1,2 or 3, and
xd4 may be 1,2, 3, 4, 5 or 6.
In an embodiment, in formula 501, ar 501 May be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthracenyl, 1, 2-benzophenanthryl, pyrenyl, etc.).
In an embodiment, in equation 501, xd4 may be 2.
In an embodiment, the fluorescent dopant may include one of compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
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[ delayed fluorescent Material ]
The emissive layer may include a delayed fluorescent material.
In the specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescent material included in the emission layer may be used as a host or as a dopant depending on the type of other materials included in the emission layer.
In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be in the range of about 0eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus, the light emitting device 10 may have improved light emitting efficiency.
In an embodiment, the delayed fluorescent material may include: containing at least one electron donor (e.g. pi-electron rich C 3 -C 60 Cyclic groups and the like, such as carbazolyl) and at least one electron acceptor (e.g., sulfoxide, cyano, pi electron deficient nitrogen-containing C 1 -C 60 Cyclic groups, etc.); or C comprising a cyclic group containing at least two boron (B) which are condensed with each other and are simultaneously shared 8 -C 60 Materials of polycyclic groups, and the like.
Examples of the delayed fluorescent material may include at least one of the compounds DF1 to DF 10:
[ Quantum dots ]
The emissive layer may comprise quantum dots.
In the specification, the quantum dot may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal.
The diameter of the quantum dots may be in the range of, for example, about 1nm to about 10 nm.
The quantum dots may be synthesized by wet chemical processes, metal organic chemical vapor deposition processes, molecular beam epitaxy processes, or any process similar thereto.
Wet chemical processes are methods that may include mixing a precursor material with an organic solvent and growing quantum dot particle crystals. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystal and controls the growth of the crystal, so that the growth of the quantum dot particle crystal can be controlled by a less costly process and can be more easily performed than vapor deposition methods such as Metal Organic Chemical Vapor Deposition (MOCVD) or Molecular Beam Epitaxy (MBE).
The quantum dots may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV elements, or compounds, or any combination thereof.
Examples of the group II-VI semiconductor compound may include: binary compounds such as CdS, cdSe, cdTe, znS, znSe, znTe, znO, hgS, hgSe, hgTe, mgSe and MgS, etc.; ternary compounds such as CdSeS, cdSeTe, cdSTe, znSeS, znSeTe, znSTe, hgSeS, hgSeTe, hgSTe, cdZnS, cdZnSe, cdZnTe, cdHgS, cdHgSe, cdHgTe, hgZnS, hgZnSe, hgZnTe, mgZnSe and MgZnS, etc.; quaternary compounds such as CdZnSeS, cdZnSeTe, cdZnSTe, cdHgSeS, cdHgSeTe, cdHgSTe, hgZnSeS, hgZnSeTe and HgZnSTe, etc.; or any combination thereof.
Examples of the group III-V semiconductor compound may include: binary compounds such as GaN, gaP, gaAs, gaSb, alN, alP, alAs, alSb, inN, inP, inAs and InSb, etc.; ternary compounds such as GaNP, gaNAs, gaNSb, gaPAs, gaPSb, alNP, alNAs, alNSb, alPAs, alPSb, inGaP, inNP, inAlP, inNAs, inNSb, inPAs and InPSb, etc.; quaternary compounds such as GaAlNP, gaAlNAs, gaAlNSb, gaAlPAs, gaAlPSb, gaInNP, gaInNAs, gaInNSb, gaInPAs, gaInPSb, inAlNP, inAlNAs, inAlNSb, inAlPAs and InAlPSb, etc.; or any combination thereof. In an embodiment, the group III-V semiconductor compound may further include a group II element. Examples of the group III-V semiconductor compound further including the group II element may include InZnP, inGaZnP and InAlZnP and the like.
Examples of the group III-VI semiconductor compound may include: binary compounds, e.g. GaS, gaSe, ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 And InTe, etc.; ternary compounds, e.g. InGaS 3 And InGaSe 3 Etc.; or any combination thereof.
Examples of the group I-III-VI semiconductor compound may include: ternary compounds, e.g. AgInS, agInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 And AgAlO 2 Etc.; or any combination thereof.
Examples of the group IV-VI semiconductor compounds may include: binary compounds such as SnS, snSe, snTe, pbS, pbSe and PbTe, etc.; ternary compounds such as SnSeS, snSeTe, snSTe, pbSeS, pbSeTe, pbSTe, snPbS, snPbSe and SnPbTe, etc.; quaternary compounds such as SnPbSSe, snPbSeTe and SnPbSTe, etc.; or any combination thereof.
Examples of group IV elements or compounds may include: single element materials such as Si and Ge; binary compounds such as SiC and SiGe, etc.; or any combination thereof.
Each element included in the multi-element compound (such as a binary compound, a ternary compound, or a quaternary compound) may be present in the particles in a uniform concentration or a non-uniform concentration.
In embodiments, the quantum dot may have a single structure (in which the concentration of each element in the quantum dot is uniform), or the quantum dot may have a core-shell structure. In an embodiment, in the case where the quantum dot has a core-shell structure, a material included in the core and a material included in the shell may be different from each other.
The shell of the quantum dot may serve as a protective layer that prevents chemical denaturation of the core to maintain semiconductor properties, and/or may serve as a charge layer that imparts electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of the material present in the shell decreases toward the core.
Quantum dotExamples of the shell of (c) may include a metal oxide, a metalloid oxide, a non-metal oxide, a semiconductor compound, or any combination thereof. Examples of metal oxides, metalloid oxides, or non-metal oxides may include: binary compounds, e.g. SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 、Mn 3 O 4 、CuO、FeO、Fe 2 O 3 、Fe 3 O 4 、CoO、Co 3 O 4 NiO, and the like; ternary compounds, e.g. MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 And CoMn 2 O 4 Etc.; or any combination thereof.
Examples of semiconductor compounds may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, or any combination thereof, as described herein. Examples of the semiconductor compound may include CdS, cdSe, cdTe, znS, znSe, znTe, znSeS, znTeS, gaAs, gaP, gaSb, hgS, hgSe, hgTe, inAs, inP, inGaP, inSb, alAs, alP, alSb or any combination thereof.
The quantum dots may have a full width at half maximum (FWHM) of the emission wavelength spectrum equal to or less than about 45 nm. For example, the quantum dots may have a FWHM of the emission wavelength spectrum equal to or less than about 40 nm. For example, the quantum dots may have a FWHM of the emission wavelength spectrum equal to or less than about 30 nm. When the FWHM of the quantum dot is within any of these ranges, the quantum dot may have improved color purity or color reproducibility. Light emitted by the quantum dots can be emitted in all directions, so that a wide viewing angle can be improved.
In embodiments, the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
Since the energy band gap can be adjusted by controlling the size of the quantum dot, light having various wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light emitting device that emits light of various wavelengths can be realized. In an embodiment, the size of the quantum dots may be selected to emit red, green, and/or blue light. In an embodiment, the size of the quantum dots may be selected to emit white light through a combination of light of various colors.
[ Electron transport region in interlayer 130 ]
The electron transport region may have a structure composed of layers (composed of a single material), a structure composed of layers including a plurality of materials different from each other, or a structure including a plurality of layers including a plurality of materials different from each other.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
In an embodiment, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein layers of each structure may be stacked in their respective stated order from the emission layer, but the structure of the electron transport region is not limited thereto.
In embodiments, the electron transport region (e.g., buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a nitrogen-containing C comprising at least one pi-deficient electron 1 -C 60 Metal-free compounds of cyclic groups.
In an embodiment, the electron transport region may include a compound represented by formula 601:
[ 601]
[Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 。
In the formula (601) of the present invention,
Ar 601 and L 601 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xe11 may be 1, 2 or 3,
xe1 may be 0, 1, 2, 3, 4 or 5,
R 601 can be unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, -Si (Q) 601 )(Q 602 )(Q 603 )、-C(＝O)(Q 601 )、-S(＝O) 2 (Q 601 ) or-P (=O) (Q 601 )(Q 602 )，
Q 601 To Q 603 Can be each independently from reference Q 1 The same is described with respect to the case,
xe21 may be 1, 2, 3, 4 or 5, and
Ar 601 、L 601 and R is 601 At least one of which may each independently be unsubstituted or substituted with at least one R 10a Substituted pi electron deficient nitrogen containing C 1 -C 60 A cyclic group.
For example, in formula 601, when xe11 is 2 or greater, two or more Ar' s 601 Can be connected to each other via a single bond.
In an embodiment, in formula 601, ar 601 Can be unsubstituted or substituted by at least one R 10a Substituted anthracenyl groups.
In an embodiment, the electron transport region may include a compound represented by formula 601-1:
[ 601-1]
In the formula (601-1),
X 614 can be N or C (R) 614 )，X 615 Can be N or C (R) 615 )，X 616 Can be N or C (R) 616 ) And X 614 To X 616 At least one of which may each be N,
L 611 to L 613 Can be each independently from reference L 601 The same is described with respect to the case,
xe611 to xe613 may each be independently the same as described with reference to xe1,
R 611 To R 613 Can be each independently from reference R 601 The descriptions are the same, and
R 614 to R 616 Can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group.
In embodiments, in formulas 601 and 601-1, xe1 and xe611 to xe613 may each be independently 0, 1, or 2.
The electron transport region may include one of the compounds ET1 to ET45, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), alq 3 BAlq, TAZ, NTAZ or any combination thereof:
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the electron transport region may have a thickness of aboutTo about->Within a range of (2). For example, the thickness of the electron transport region may be about +.>To about->Within a range of (2). When the electron transport region comprises a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be about>To about->And the thickness of the electron transport layer may be within the range of about +.>To about->Within a range of (2). For example, the thickness of the buffer layer, hole blocking layer or electron control layer may each independently be about +. >To about->Within a range of (2). For example, the thickness of the electron transport layer may be about +.>To about->Within a range of (2). When the buffer layer, hole blocking layer, electron control layer, electron transport layer and/or electron transport layerWhen the thickness of the transfer region is within these ranges, satisfactory electron transfer characteristics can be obtained without significantly increasing the driving voltage.
In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further comprise a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may Be Li ion, na ion, K ion, rb ion or Cs ion, and the metal ion of the alkaline earth metal complex may Be ion, mg ion, ca ion, sr ion or Ba ion.
The ligands coordinated to the metal ion of the alkali metal complex or to the metal ion of the alkaline earth metal complex may each independently comprise hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
For example, the metal-containing material may include a lithium (Li) complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
The electron injection layer may have a structure composed of layers (composed of a single material), a structure composed of layers including different materials, or a structure including a plurality of layers including different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may comprise Li, na, K, rb, cs or any combination thereof. The alkaline earth metal may include Mg, ca, sr, ba or any combination thereof. The rare earth metal may include Sc, Y, ce, tb, yb, gd or any combination thereof.
The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound can be an alkali metal, alkaline earth metal, oxide of a rare earth metal, halide (e.g., fluoride, chloride, bromide, iodide, etc.), or telluride, or any combination thereof.
The alkali metal-containing compound may include: alkali metal oxides, e.g. Li 2 O、Cs 2 O and K 2 O, etc.; alkali metal halides such as LiF, naF, csF, KF, liI, naI, csI and KI, etc.; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal oxide, such as BaO, srO, caO, ba x Sr 1-x O (where x is a real number satisfying 0<x<1) And Ba (beta) x Ca 1-x O (where x is a real number satisfying 0<x<1) Etc. The rare earth-containing metal compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 Or any combination thereof. In embodiments, the rare earth-containing compound may include a lanthanide metal telluride. Examples of lanthanide metal telluride may include LaTe, ceTe, prTe, ndTe, pmTe, smTe, euTe, gdTe, tbTe, dyTe, hoTe, erTe, tmTe, ybTe, luTe, la 2 Te 3 、Ce 2 Te 3 、Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 、Gd 2 Te 3 、Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 、Er 2 Te 3 、Tm 2 Te 3 、Yb 2 Te 3 And Lu 2 Te 3 Etc.
The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion, and a ligand (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof) that binds to the metal ion.
In an embodiment, as described above, the electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by formula 601).
In embodiments, the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide) and an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI: yb co-deposited layer, a RbI: yb co-deposited layer, or the like.
When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix including the organic material.
The electron injection layer may have a thickness of aboutTo about->Within a range of (2). For example, the thickness of the electron injection layer may be about +.>To about->Within a range of (2). When the thickness of the electron injection layer is within any of the above ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[ second electrode 150]
The second electrode 150 may be disposed on the interlayer 130 having the above-described structure. The second electrode 150 may be a cathode as an electron injection electrode. The material used to form the second electrode 150 may be a material having a low work function, for example, a metal, an alloy, a conductive compound, or any combination thereof.
The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multi-layer structure.
[ capping layer ]
The light emitting device 10 may include a first capping layer disposed outside the first electrode 110 and/or a second capping layer disposed outside the second electrode 150. For example, the light emitting device 10 may have: a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order.
Light generated in the emission layer of the interlayer 130 of the light emitting device 10 may pass through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and be extracted toward the outside through the first capping layer. Light generated in the emission layer of the interlayer 130 of the light emitting device 10 may pass through the second electrode 150, which may be a semi-transmissive electrode or a transmissive electrode, and be extracted toward the outside through the second capping layer.
The first capping layer and the second capping layer may each increase external emission efficiency according to principles of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be improved.
The first capping layer and the second capping layer may each comprise a material having a refractive index greater than or equal to about 1.6 (relative to a wavelength of about 589 nm).
The first capping layer and the second capping layer may each be independently an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer and the second capping layer may each independently comprise a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amine-containing compound may be optionally substituted with a substituent containing O, N, S, se, si, F, cl, br, I or any combination thereof.
In embodiments, at least one of the first capping layer and the second capping layer may each independently include an amine-containing compound.
In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.
In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of compounds HT28 through HT33, one of compounds CP1 through CP6, β -NPB, or any combination thereof:
[ film ]
At least one of the amine compounds represented by formulas 1 to 4 may be included in various films. Accordingly, another aspect provides a film that may include at least one of the amine compounds represented by formulas 1 to 4. The film may be, for example, an optical member (or light control device) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarizing layer, or a quantum dot layer, etc.), a light blocking member (e.g., a light reflection layer, a light absorption layer, etc.), or a protective member (e.g., an insulating layer, a dielectric layer, etc.).
[ electronic device ]
The light emitting device may be included in various electronic apparatuses. In an embodiment, the electronic device including the light emitting device may be a light emitting device, an authentication device, or the like.
In addition to the light emitting apparatus, the electronic device (e.g., light emitting device) may further include: a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one traveling direction of light emitted from the light emitting device. In an embodiment, the light emitted from the light emitting device may be blue light or white light. The light emitting device may be the same as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots described herein.
The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixels, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixels, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixels.
The pixel defining layer may be disposed between the plurality of sub-pixels to define each sub-pixel.
The color filter may further include a plurality of color filter regions and a light shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern disposed between the plurality of color conversion regions.
The color filter region (or color conversion region) may include a first region that emits first color light, a second region that emits second color light, and/or a third region that emits third color light, wherein the first, second, and/or third color light may have maximum emission wavelengths that are different from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. For example, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the same as described herein. The first region, the second region and/or the third region may each further comprise a diffuser.
In an embodiment, the light emitting device may emit first light, the first region may absorb the first light to emit first-first color light, the second region may absorb the first light to emit second-first color light, and the third region may absorb the first light to emit third-first color light. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
In addition to the light emitting device as described herein, the electronic apparatus may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of a first electrode and a second electrode of the light emitting device.
The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
The electronic apparatus may further include a sealing portion for sealing the light emitting device. The sealing portion may be disposed between the color filter and/or the color conversion layer and the light emitting device. The sealing portion may allow light from the light emitting device to be extracted to the outside, and may simultaneously prevent ambient air and moisture from penetrating into the light emitting device. The sealing part may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
Depending on the use of the electronic device, various functional layers may be further included on the sealing portion in addition to the color filter and/or the color conversion layer. Examples of functional layers may include touch screen layers, polarizing layers, authentication devices, and the like. The touch screen layer may be a pressure sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., a fingertip, a pupil, etc.).
The authentication apparatus may further include a biometric information collector in addition to the light emitting device as described above.
The electronic device can be applied to various displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring apparatuses, pulse wave measuring apparatuses, electrocardiogram displays, ultrasonic diagnostic apparatuses, or endoscope displays), fish probes, various measuring tools, meters (e.g., meters for vehicles, aircraft, and watercraft), projectors, and the like.
[ description of FIGS. 2 and 3 ]
Fig. 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
The electronic apparatus of fig. 2 includes a substrate 100, a Thin Film Transistor (TFT), a light emitting device, and a package portion 300 sealing the light emitting device.
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent impurities from penetrating through the substrate 100 and may provide a flat surface on the substrate 100.
The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220, and the gate electrode 240 may be disposed on the gate insulating film 230.
An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and may be disposed between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source and drain regions of the active layer 220, and the source and drain electrodes 260 and 270 may contact the exposed portions of the source and drain regions of the active layer 220, respectively.
The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device may be provided on the passivation layer 280. The light emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may not entirely cover the drain electrode 270 and may expose a portion of the drain electrode 270, and the first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or a polyacrylic acid organic film. Although not shown in fig. 2, at least some of the layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290, provided in the form of a common layer.
The second electrode 150 may be disposed on the interlayer 130, and the capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be disposed on the capping layer 170. The encapsulation portion 300 may be disposed on the light emitting device to protect the light emitting device from moisture and/or oxygen. The encapsulation part 300 may include: an inorganic film comprising silicon nitride (SiN x ) Silicon oxide (SiO) x ) Indium tin oxide, indium zinc oxide, or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyaromatic ester, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, or the like), an epoxy resin (e.g., aliphatic Glycidyl Ether (AGE), or the like), or any combination thereof; or any combination of inorganic and organic films.
Fig. 3 is a schematic cross-sectional view of an electronic device according to another embodiment.
The electronic device of fig. 3 may be different from the electronic device of fig. 2 at least in that the light shielding pattern 500 and the functional region 400 are further included on the encapsulation part 300. The functional area 400 may be: a color filter region, a color conversion region, or a combination of a color filter region and a color conversion region. In an embodiment, the light emitting device included in the electronic apparatus of fig. 3 may be a tandem light emitting device.
[ method of production ]
The layers included in the hole transport region, the emission layer, and the layers included in the electron transport region may be formed in some regions by using one or more suitable methods selected from vacuum deposition, spin coating, casting, langmuir-blodgett (LB) deposition, inkjet printing, laser induced thermal imaging, and the like.
When the layers included in the hole transport region, the emission layer, and the layers included in the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100 to about 500 c, about 10 -8 To about 10 -3 Vacuum level of the tray and the likePer second to about->The deposition rate/sec, depending on the material to be included in the layer to be formed and the structure of the layer to be formed.
[ definition of terms ]
The term "C" as used herein 3 -C 60 Carbocyclyl "may be a cyclic group consisting of only carbon atoms as the only ring-forming atoms and having 3 to 60 carbon atoms, such as C 5 -C 60 Carbocyclyl and C 5 -C 30 Carbocyclyl; and the term "C" as used herein 1 -C 60 The heterocyclic group "may be a cyclic group having 1 to 60 carbon atoms and further having at least one hetero atom as a ring-forming atom in addition to the carbon atoms, such as C 1 -C 30 A heterocyclic group. C (C) 3 -C 60 Carbocyclyl and C 1 -C 60 The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, C 1 -C 60 The number of ring forming atoms in the heterocyclyl may be from 3 to 61.
The term "cyclic group" as used herein may include C 3 -C 60 Carbocyclyl or C 1 -C 60 Both heterocyclic groups.
The term "pi-electron rich C" as used herein 3 -C 60 The cyclic group "may be a cyclic group having 3 to 60 carbon atoms and may not include = -N' as a ring forming moiety, and the term" pi electron deficient nitrogen-containing C "as used herein 1 -C 60 The cyclic group "may be a heterocyclic group having 1 to 60 carbon atoms and may include = -N' as a ring forming moiety.
In the present embodiment of the present invention,
C 3 -C 60 Carbocyclyl may be a T1 group, or a group in which two or more T1 groups are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentylene, naphthyl, azulenyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, perylenyl, pentylphenyl, heptenyl, tetracenyl, picenyl, naphthacene, pentacenyl, yuzuo, coroneyl, egg phenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenofrenyl, or indenoanthrenyl),
C 1 -C 60 the heterocyclic group may be a T2 group, a group in which at least two T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphtoindolyl, isoindolyl, benzisoindolyl, naphthyridoneisoindolyl, benzothiophenyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilol, dibenzothienyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzofuranyl, and benzofuranyl benzothiophene carbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthafuranyl, benzonaphthacene thienyl, benzonaphthacene, benzofurandibenzofuranyl, benzofurandibenzobenzothiophenyl, benzothiophene dibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthroline, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilol, azadibenzothienyl or azadibenzofuranyl, and the like),
Pi electron rich C 3 -C 60 The cyclic group may be: a T1 group, a group in which at least two T1 groups are fused to each other, a T3 group, a group in which at least two T3 groups are fused to each other, or a group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C 3 -C 60 Carbocyclyl, 1H-pyrrolyl, silol, borolopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthaindolyl, isoindolylIndolyl, benzisoindolyl, naphthyridinyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzosilol, dibenzothienyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofurancarbazolyl, benzothiocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphtalenofuranyl, benzonaphtalenothienyl, benzonaphtalenosollyl, benzodibenzofuranyl, benzodibenzodibenzothiophenyl, or benzothiophenyldibenzothiophenyl, etc.), and
pi electron deficient nitrogen containing C 1 -C 60 The cyclic group may be: a T4 group, a group in which at least two T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group and at least one T3 group are fused to each other (for example, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzoquinoxalinyl group, a benzoquinazolinyl group, a pyrrolyl group, a cinnolinyl group, an imidazolyl group, a naphthyridinyl group, an imidazoyl group, a naphthyridinyl group, a pyrrolizinyl group, a diazolidinyl group, a etc.),
Wherein the T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutenyl group, a cyclopentene group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptenyl group, an adamantane group, a norbornane (or bicyclo [2.2.1] heptane) group, a norbornenyl group, a bicyclo [1.1.1] pentane group, a bicyclo [2.1.1] hexane group, a bicyclo [2.2.2] octane group, or a phenyl group,
t2 groups may be furyl, thienyl, 1H-pyrrolyl, silol, borol, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilol, azaborol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl or dihydropyridazinyl,
the T3 group may be furyl, thienyl, 1H-pyrrolyl, silol or borolopentadienyl, and
The T4 group may be a 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilol, azaborol, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl group.
The terms "cyclic group", "C", as used herein 3 -C 60 Carbocyclyl "," C 1 -C 60 Heterocyclyl "," pi-electron rich C 3 -C 60 The cyclic group "or" pi electron deficient nitrogen-containing C 1 -C 60 The cyclic groups "may each be a group condensed with any cyclic group, monovalent group, or multivalent group (e.g., divalent group, trivalent group, tetravalent group, etc.) according to the structure of the general formula in which the corresponding term is used. For example, a "phenyl" may be a benzo, phenyl, phenylene, or the like, which may be readily understood by one of ordinary skill in the art according to structures of the formula including "phenyl".
Monovalent C 3 -C 60 Carbocyclyl and monovalent C 1 -C 60 Examples of heterocyclyl groups may include C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups. Divalent C 3 -C 60 Carbocyclyl and divalent C 1 -C 60 Examples of heterocyclyl groups may include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenyl ene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene group, C 1 -C 60 Heteroarylene, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups.
The term "C" as used herein 1 -C 60 The alkyl "may be a straight or branched aliphatic hydrocarbon monovalent radical having 1 to 60 carbon atoms, such as C 1 -C 30 Alkyl, C 1 -C 20 Alkyl and C 1 -C 10 Alkyl groups, and examples thereof may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji and tert-decyl. The term "C" as used herein 1 -C 60 The alkylene group "may be a group having a group corresponding to C 1 -C 60 Divalent groups of substantially the same structure as the alkyl groups.
The term "C" as used herein 2 -C 60 Alkenyl "can be at C 2 -C 60 Monovalent hydrocarbon groups having at least one carbon-carbon double bond in the middle or at the end of the alkyl group, e.g. C 2 -C 30 Alkenyl and C 2 -C 10 Alkenyl groups, and examples thereof may include ethenyl, propenyl, butenyl, and the like. The term "C" as used herein 2 -C 60 Alkenylene radicals "may be those having a radical corresponding to C 2 -C 60 Alkenyl groups are divalent radicals of substantially the same structure.
The term "C" as used herein 2 -C 60 Alkynyl "can be at C 2 -C 60 Monovalent hydrocarbon groups having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, and examples thereof may include acetylene groups, propynyl groups, and the like. The term "C" as used herein 2 -C 60 Alkynylene "may be of the same structure as C 2 -C 60 Alkynyl groups are divalent groups of substantially the same structure.
The term "C" as used herein 1 -C 60 Alkoxy "may be represented by-O (A) 101 ) (wherein A 101 Can be C 1 -C 60 Alkyl) represented by a monovalent group such as C 1 -C 10 Alkoxy groups, and examples thereof may include methoxy, ethoxy, and isopropoxy groups, and the like.
The term "C" as used herein 3 -C 10 Cycloalkyl "may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo [2.2.1]Heptyl), bicyclo [1.1.1]Amyl, bicyclo [2.1.1 ]]Hexyl and bicyclo [2.2.2]Octyl, and the like. The term "C" as used herein 3 -C 10 Cycloalkylene radicals "may be those having a radical corresponding to C 3 -C 10 Cycloalkyl groups are essentially the same structural divalent groups.
The term "C" as used herein 1 -C 10 The heterocycloalkyl group "may be a monovalent cyclic group of 1 to 10 carbon atoms further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof may include 1,2,3, 4-oxatriazolyl, tetrahydrofuranyl, tetrahydrothienyl, and the like. The term "C" as used herein 1 -C 10 Heterocyclylene "may be of the same order as C 1 -C 10 Divalent groups of substantially the same structure as the heterocycloalkyl group.
The term "C" as used herein 3 -C 10 Cycloalkenyl "may be a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and no aromaticity, and examples thereof may beIncluding cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. The term "C" as used herein 3 -C 10 Cycloalkenyl "may be of the formula C 3 -C 10 Divalent groups of substantially identical structure of cycloalkenyl groups.
The term "C" as used herein 1 -C 10 The heterocycloalkenyl "may be a monovalent cyclic group of 1 to 10 carbon atoms, which further includes at least one ring-forming atom as a heteroatom in addition to the carbon atoms, and has at least one double bond in its cyclic structure. C (C) 1 -C 10 Examples of heterocycloalkenyl groups may include 4, 5-dihydro-1, 2,3, 4-oxazolyl, 2, 3-dihydrofuranyl, 2, 3-dihydrothiophenyl, and the like. The term "C" as used herein 1 -C 10 Heterocycloalkenylene "may be a heterocyclic ring having a group corresponding to C 1 -C 10 A divalent group of substantially the same structure as the heterocycloalkenyl group.
The term "C" as used herein 6 -C 60 Aryl "may be a monovalent radical of a carbocyclic aromatic system having 6 to 60 carbon atoms, such as C 6 -C 10 Aryl, and the term "C" as used herein 6 -C 60 Arylene "may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. C (C) 6 -C 60 Examples of aryl groups may include phenyl, pentylene, naphthyl, azulenyl, indacenyl, acenaphthylene, phenalkenyl, phenanthrene, anthryl, fluoranthenyl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, perylene, pentylphenyl, heptenyl, tetracenyl, picene, hexaphenyl, pentacenyl, yuzuo, coronenyl, and egg phenyl groups, and the like. When C 6 -C 60 Aryl and C 6 -C 60 Where arylene groups each independently include two or more rings, the individual rings may be fused to one another.
The term "C" as used herein 1 -C 60 Heteroaryl "may be a monovalent radical of a heterocyclic aromatic system having 1 to 60 carbon atoms, further comprising at least one heteroatom as a ring-forming atom in addition to carbon atoms. The term "C" as used herein 1 -C 60 Heteroarylene "may be a compound having 1 to 60 carbon atomsThe divalent group of the heterocyclic aromatic system further comprises at least one heteroatom as a ring forming atom in addition to carbon atoms. C (C) 1 -C 60 Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl and naphthyridinyl. When C 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each independently include two or more rings, the rings may be fused to each other.
The term "monovalent non-aromatic fused polycyclic group" as used herein may be a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, with only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenofenyl, indenoanthrenyl, and the like. The term "divalent non-aromatic fused polycyclic group" as used herein may be a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic groups described above.
The term "monovalent non-aromatic fused heteropolycyclic group" as used herein may be a monovalent group having two or more rings fused to each other (e.g., having 1 to 60 carbon atoms), further comprising at least one heteroatom in addition to carbon atoms as a ring-forming atom and being non-aromatic in its entire molecular structure. Examples of monovalent non-aromatic fused heterocyclic groups may include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthaindolyl, isoindolyl, benzisoindolyl, naphthaisoindolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiazyl, dibenzothienyl, dibenzofuranyl, azacarbazolyl, azafluorene, azadibenzothiazyl, azadibenzothienyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolocarbazolyl, benzocarbazolyl, benzofuranyl, benzothiophenyl, and naphthazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein may be a divalent group having substantially the same structure as the monovalent non-aromatic fused heteropolycyclic groups described above.
The term "C" as used herein 6 -C 60 Aryloxy "may be represented by-O (A) 102 ) (wherein A 102 Can be C 6 -C 60 Aryl) and the term "C" as used herein 6 -C 60 Arylthio "may be represented by-S (A) 103 ) (wherein A 103 Can be C 6 -C 60 Aryl) groups.
The term "C" as used herein 7 -C 60 Aralkyl "may be represented by- (A) 104 )(A 105 ) (wherein A 104 Can be C 1 -C 54 Alkylene group, and A 105 Can be C 6 -C 59 Aryl) and the term "C" as used herein 2 -C 60 The heteroaralkyl group "may be represented by- (A) 106 )(A 107 ) (wherein A 106 Can be C 1 -C 59 Alkylene group, and A 107 Can be C 1 -C 59 Heteroaryl) groups.
In the specification, the group "R 10a "can be:
deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 )。
In the specification, Q 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently can be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
The term "heteroatom" as used herein may be any atom other than a carbon atom or a hydrogen atom. Examples of heteroatoms may include O, S, N, P, si, B, ge, se or any combination thereof.
The term "third row transition metal" as used herein may include Hf, ta, W, re, os, ir, pt or Au, or the like.
The term "Ph" as used herein refers to phenyl; the term "Me" as used herein refers to methyl; the term "Et" as used herein refers to ethyl; the term "tert-Bu" or "Bu" as used herein t "each refers to a tert-butyl group; and the term "OMe" as used herein refers to methoxy.
The term "biphenyl" as used herein may be "phenyl substituted with phenyl". For example, "biphenyl" may be a compound having C 6 -C 60 Substituted phenyl groups with aryl groups as substituents.
The term "terphenyl" as used herein may be "phenyl substituted with biphenyl". For example, "terphenyl" may be a compound having a quilt C 6 -C 60 Aryl substituted C 6 -C 60 Substituted phenyl groups with aryl groups as substituents.
Unless otherwise defined, the symbols as used herein and each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
The compound according to the embodiment and the light emitting device according to the embodiment will be described in detail below with reference to the following synthesis examples and examples. The expression "using B instead of a" used in describing the synthesis examples means that the same molar equivalent of B is used instead of a.
Examples (example)
Synthesis example
Synthesis example 1: synthesis of Compound 1
1. Synthesis of intermediate 1a
2-bromo-9-phenyl-9H-carbazole (1 eq.), aniline (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 1a. (yield: 85%)
2. Synthesis of Compound 1
Intermediate 1a (1 eq.), 2-bromo-9, 9-diphenyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 1 was obtained. ( Yield: 86%, HRMS (ESI) (high resolution mass spectrometry (electrospray ionization)): calculated values: 650.2722; measurement value: 650.2720 )
Synthesis example 2: synthesis of Compound 3
1. Synthesis of intermediate 3a
(4-bromophenyl) (phenyl) methanone (1.0 eq.), phenylboronic acid (1.0 eq.), tetrakis (triphenylphosphine) palladium (0.05 eq.) and potassium carbonate (2.0 eq.) were dissolved in a solution containing THF and H mixed in a 4:1 volume ratio 2 O, and stirred at 90 ℃ under nitrogen atmosphere for 12 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 3a. (yield: 62%)
2. Synthesis of intermediate 3b
2-bromo-4 '-chloro-1, 1' -biphenyl (1.0 eq.) and tetrahydrofuran were cooled to-78 ℃ while stirring. N-butyllithium (1.1 eq.) was slowly added dropwise to the mixed solution and stirred at-78 ℃ for 1 hour. Intermediate 3a (1.1 eq.) was slowly added dropwise thereto at-78 ℃ and stirred at room temperature for 4 hours to obtain a reaction mixture. It was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 3b. (yield: 69%)
3. Synthesis of intermediate 3c
Intermediate 3b (1.0 eq.) was dissolved in a solution containing acetic acid and hydrochloric acid in a volume ratio of 9:1 and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained is dried and then Drying again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 3c. (yield: 69%)
4. Synthesis of Compound 3
Intermediate 3c (1 eq.), intermediate 1a (1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 3 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 726.3035; measurement value: 726.3037 )
Synthesis example 3: synthesis of Compound 7
1. Synthesis of intermediate 7a
2-bromo-9H-carbazole (1 eq.), 4-iodo-1, 1' -biphenyl (1 eq.), copper (I) iodide (0.03 eq.) and potassium carbonate (2.0 eq.) were dissolved in Dimethylformamide (DMF) and stirred at 120 ℃ under nitrogen atmosphere for 8 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 7a.
2. Synthesis of intermediate 7b
Intermediate 7a (1 eq.), aniline (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, by using ethyl acetateThe ethyl acetate and water were subjected to three extraction processes each, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 7b. (yield: 85%)
3. Synthesis of Compound 7
Intermediate 7b (1 eq.), 2-bromo-9, 9-diphenyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 7 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 726.3035; measurement value: 726.3030 )
Synthesis example 4: synthesis of Compound 15
1. Synthesis of intermediate 15a
(3-bromophenyl) (phenyl) methanone (1.0 eq.), phenylboronic acid (1.0 eq.), tetrakis (triphenylphosphine) palladium (0.05 eq.) and potassium carbonate (2.0 eq.) were dissolved in a solution containing THF and H mixed in a 4:1 volume ratio 2 O, and stirred at 90 ℃ under nitrogen atmosphere for 12 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 15a. (yield: 62%)
2. Synthesis of intermediate 15b
Stirring 2-bromo-4 '-chloro-1, 1'-biphenyl (1.0 eq.) and tetrahydrofuran were cooled to-78 ℃. N-butyllithium (1.1 eq) was slowly added dropwise to the mixed solution and stirred at-78 ℃ for 1 hour. Intermediate 15a (1.1 eq.) was slowly added dropwise thereto at-78 ℃ and stirred at room temperature for 4 hours to obtain a reaction mixture. It was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 15b. (yield: 69%)
3. Synthesis of intermediate 15c
Intermediate 15b (1.0 eq.) was dissolved in a solution containing acetic acid and hydrochloric acid in a volume ratio of 9:1 and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 15c. (yield: 69%)
4. Synthesis of intermediate 15d
Intermediate 15c (1 eq.), 1-aminonaphthalene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 15d. (yield: 85%)
5. Synthesis of Compound 15
Intermediate 15d (1 eq.), 2-bromo-9-phenyl-9H-carbazole (1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ for 2 hours in a nitrogen atmosphere to obtain the reactionThe mixture should be mixed. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 15 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 776.3191; measurement value: 776.3189 )
Synthesis example 5: synthesis of Compound 83
1. Synthesis of intermediate 83a
(2-bromophenyl) (phenyl) methanone (1.0 eq.), phenylboronic acid (1.0 eq.), tetrakis (triphenylphosphine) palladium (0.05 eq.) and potassium carbonate (2.0 eq.) were dissolved in a solution containing THF and H mixed in a 4:1 volume ratio 2 O, and stirred at 90 ℃ under nitrogen atmosphere for 12 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 83a was obtained. (yield: 62%)
2. Synthesis of intermediate 83b
2-bromo-4 '-chloro-1, 1' -biphenyl (1.0 eq) and tetrahydrofuran were cooled to-78 ℃ while stirring. N-butyllithium (1.1 eq) was slowly added dropwise to the mixed solution and stirred at-78 ℃ for 1 hour. Intermediate 83a (1.1 eq.) was slowly added dropwise thereto at-78 ℃ and stirred at room temperature for 4 hours to obtain a reaction mixture. It was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 83b was obtained. (yield: 69%)
3. Synthesis of intermediate 83c
Intermediate 83b (1.0 eq.) was dissolved in a solution containing acetic acid and hydrochloric acid in a volume ratio of 9:1 and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 83c was obtained. (yield: 69%)
4. Synthesis of intermediate 83d
2-bromo-9H-carbazole (1 eq.), 2-iodo-1, 1' -biphenyl (1 eq.), copper (I) iodide (0.03 eq.) and potassium carbonate (2.0 eq.) were dissolved in DMF and stirred at 120 ℃ under nitrogen atmosphere for 8 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 83d was obtained.
5. Synthesis of intermediate 83e
Intermediate 83d (1 eq.), 2-aminonaphthalene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 83e was obtained. (yield: 85%)
6. Synthesis of Compound 83
Intermediate 83e (1 eq.), intermediate 83c (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, by using The ethyl acetate and water were subjected to three extraction processes each, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 83 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 852.3504; measurement value: 852.3506 )
Synthesis example 6: synthesis of Compound 92
1. Synthesis of intermediate 92a
2-bromo-9H-carbazole (1 eq.), 3-iodo-1, 1' -biphenyl (1 eq.), copper (I) iodide (0.03 eq.) and potassium carbonate (2.0 eq.) were dissolved in DMF and stirred at 120 ℃ under nitrogen atmosphere for 8 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 92a.
2. Synthesis of intermediate 92b
Intermediate 92a (1 eq.), 2-aminonaphthalene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 92b. (yield: 85%)
3. Synthesis of Compound 92
Intermediate 92b (1 eq.), intermediate 83c (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.), and sodium tert-butoxide (2.0 eq.) were dissolvedThe reaction mixture was obtained by dissolving in toluene and stirring at 80℃under nitrogen atmosphere for 2 hours. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 92 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 852.3504; measurement value: 852.3508 )
Synthesis example 7: synthesis of Compound 94
1. Synthesis of intermediate 94a
Naphthalene-2-boronic acid (1.0 eq.), 1, 3-diiodobenzene (1.0 eq.), tetrakis (triphenylphosphine) palladium (0.05 eq.) and potassium carbonate (2.0 eq.) were dissolved in a solution containing THF and H mixed in a 4:1 volume ratio 2 O, and stirred at 90 ℃ under nitrogen atmosphere for 12 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 94a was obtained. (yield: 62%)
2. Synthesis of intermediate 94b
3-bromo-9H-carbazole (1 eq.), intermediate 94a (1 eq.), copper (I) iodide (0.03 eq.) and potassium carbonate (2.0 eq.) were dissolved in DMF and stirred at 120 ℃ under nitrogen atmosphere for 8 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 94b.
3. Synthesis of intermediate 94c
Intermediate 94b (1.1 eq.)Aniline (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 94c. (yield: 86%)
4. Synthesis of Compound 94
Intermediate 94c (1 eq.), 2-bromo-9, 9-dimethyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 94 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 652.2878; measurement value: 652.2880 )
Synthesis example 8: synthesis of Compound 99
1. Synthesis of intermediate 99a
3-bromo-9- (4- (naphthalen-2-yl) phenyl) -9H-carbazole (1.1 eq.), [1,1' -biphenyl]-2-amine (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. Subjecting the resulting product toColumn chromatography, thereby obtaining intermediate 99a. (yield: 86%)
2. Synthesis of Compound 99
Intermediate 99a (1 eq.), 2-bromo-9, 9-dimethyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 99 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 728.3191; measurement value: 728.3195 )
Synthesis example 9: synthesis of Compound 100
1. Synthesis of intermediate 100a
3- (4-bromophenyl) -9-phenyl-9H-carbazole (1.1 eq.), aniline (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 100a. (yield: 86%)
2. Synthesis of Compound 100
Intermediate 100a (1 eq.), 2-bromo-9, 9-dimethyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtainThe reaction mixture was obtained. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 100 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 602.2722; measurement value: 602.2724 )
Synthesis example 10: synthesis of Compound 105
1. Synthesis of intermediate 105a
3- (4-bromophenyl) -9-phenyl-9H-carbazole (1.1 eq.), [1,1' -biphenyl]-2-amine (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 105a was obtained. (yield: 86%)
2. Synthesis of Compound 105
Intermediate 105a (1 eq.), 2-bromo-9, 9-dimethyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 105 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 678.3035; measurement value: 678.3040 )
Synthesis example 11: synthesis of Compound 110
1. Synthesis of intermediate 110a
3- (3-bromophenyl) -9-phenyl-9H-carbazole (1.1 eq.), [1,1' -biphenyl]-3-amine (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 110a. (yield: 86%)
2. Synthesis of Compound 110
Intermediate 110a (1 eq.), 2-bromo-9, 9-dimethyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 110 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 678.3035; measurement value: 678.3038 )
Synthesis example 12: synthesis of Compound 113
1. Synthesis of intermediate 113a
Dibenzo [ b, d]Furan-4-ylboronic acid (1.0 eq.), 4-bromophenyl boronic acid (1.0 eq.), tetrakis (triphenylphosphine) palladium (0.05 eq.) and potassium carbonate (2.0 eq.) were dissolved in a solution containing THF and H mixed in a 4:1 volume ratio 2 O, and stirred at 90 ℃ under nitrogen atmosphere for 12 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 113a. (yield: 62%)
2. Synthesis of intermediate 113b
3-bromo-9H-carbazole (1 eq.), intermediate 113a (1 eq.), copper (I) iodide (0.03 eq.) and potassium carbonate (2.0 eq.) were dissolved in DMF and stirred at 120 ℃ under nitrogen atmosphere for 8 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 113b.
3. Synthesis of intermediate 113c
Intermediate 113b (1.1 eq.), 2-aminonaphthalene (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 113c. (yield: 86%)
4. Synthesis of Compound 113
Intermediate 113c (1 eq.), 2-bromo-9, 9-dimethyl-9H-fluorene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in tolueneAnd stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 113 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 742.2984; measurement value: 742.2988 )
Synthesis example 13: synthesis of Compound 124
1. Synthesis of intermediate 124a
9, 9-dimethyl-9H-fluoren-2-amine (1.0 eq.), 1- (4-bromophenyl) adamantane (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred under nitrogen atmosphere at 80 ℃ for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 124a. (yield: 86%)
2. Synthesis of Compound 124
Intermediate 124a (1.0 eq.) 2- (4-bromophenyl) bicyclo [2.2.1]Heptane (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 124 was obtained. (yield: 86% HRMS (ESI): calculated: 589.3709, a step of performing the process; measurement value: 589.3713)
Synthesis example 14: synthesis of Compound 147
1. Synthesis of intermediate 147a
Dibenzo [ b, d]Thiophene-3-amine (1.0 eq.), 1-bromo-4-cyclohexylbenzene (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining an intermediate 147a. (yield: 86%)
2. Synthesis of Compound 147
Intermediate 147a (1.0 eq.) and 2- (4-bromophenyl) bicyclo [2.2.1]Heptane (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 147 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 527.2647; measurement value: 527.2650 )
Synthesis example 15: synthesis of Compound 163
1. Synthesis of intermediate 163a
2-bromo-4 '-chloro-1, 1' -biphenyl (1.0 eq) and tetrahydrofuran were cooled to-78 ℃ while stirring. N-butyllithium (1.1 eq) was slowly added dropwise to the mixed solution and stirred at-78 ℃ for 1 hour. Cyclopentanone (1.1 eq.) was slowly added dropwise thereto at-78 ℃ and stirred at room temperature for 4 hours to obtain a reaction mixture. It was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 163a. (yield: 69%)
2. Synthesis of intermediate 163b
Intermediate 163a (1.0 eq.) was dissolved in a solution containing acetic acid and hydrochloric acid in a volume ratio of 9:1 and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 163b. (yield: 69%)
3. Synthesis of intermediate 163c
Intermediate 163b (1.1 eq.), 4-cyclohexylaniline (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 163c. (yield: 85%)
4. Synthesis of Compound 163
Intermediate 163c (1 eq.) 2- (4-bromophenyl) bicyclo [2.2.1]Heptane (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.), and tert-butyl phosphineSodium butoxide (2.0 eq.) was dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 163 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 563.3552; measurement value: 563.3555 )
Synthesis example 16: synthesis of Compound 181
1. Synthesis of intermediate 181a
2-bromo-4 '-chloro-1, 1' -biphenyl (1.0 eq) and tetrahydrofuran were cooled to-78 ℃ while stirring. N-butyllithium (1.1 eq) was slowly added dropwise to the mixed solution and stirred at-78 ℃ for 1 hour. Dicyclohexyl ketone (1.1 eq.) was slowly added dropwise thereto at-78 ℃ and stirred at room temperature for 4 hours to obtain a reaction mixture. It was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining an intermediate 181a.
(yield: 69%)
2. Synthesis of intermediate 181b
Intermediate 181a (1.0 eq.) was dissolved in a solution containing acetic acid and hydrochloric acid in a volume ratio of 9:1 and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining an intermediate 181b. (yield: 69%)
3. Intermediate 181cSynthesis
Intermediate 181b (1.1 eq.) and 4- (bicyclo [ 2.2.1.)]Heptane-2-yl) aniline (1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining an intermediate 181c. (yield: 85%)
4. Synthesis of Compound 181
Intermediate 181c (1 eq.) 2- (4-bromophenyl) bicyclo [2.2.1]Heptane (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 181 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 685.4648; measurement value: 685.4650 )
Synthesis example 17: synthesis of Compound 185
1. Synthesis of intermediate 185a
Stirring the 2-phenyldibenzo [ b, d]Furan (1.0 eq.) and tetrahydrofuran were cooled to-78 ℃. N-butyllithium (1.1 eq) was slowly added dropwise to the mixed solution and stirred at-78 ℃ for 1 hour. Bromine (1.2 eq.) was slowly added dropwise thereto at-78 ℃ and stirred at room temperature for 4 hours to obtain a reaction mixture. In which thiothio is added dropwiseAfter the sodium acid solution, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining an intermediate 185a. (yield: 49%)
2. Synthesis of intermediate 185b
Intermediate 185a (1.1 eq.), 4- (naphthalen-2-yl) aniline (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 185b was obtained. (yield: 86%)
3. Synthesis of Compound 185
Intermediate 185b (1 eq.), 2- (4-bromophenyl) naphthalene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 185 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 663.2562; measurement value: 663.2565 )
Synthesis example 18: synthesis of Compound 188
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1. Synthesis of intermediate 188a
4, 6-dibromodibenzo [ b, d ]]Furan (1.0 eq), phenylboronic acid (1.0 eq), tetrakis (triphenylphosphine) palladium (0.05 eq) and potassium carbonate (2.0 eq) were dissolved in a solution containing THF and H mixed in a 4:1 volume ratio 2 O, and stirred at 90 ℃ under nitrogen atmosphere for 12 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 188a. (yield: 62%)
2. Synthesis of intermediate 188b
Intermediate 188a (1.1 eq.), 3- (naphthalen-2-yl) aniline (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 188b. (yield: 86%)
3. Synthesis of Compound 188
Intermediate 188b (1.0 eq.), 1- (4-bromophenyl) naphthalene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 188 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 663.2562; measurement value: 663.2560 )
Synthesis example 19: synthesis of Compound 194
1. Synthesis of intermediate 194a
2-bromodibenzo [ b, d ]]Furan (1.0 eq), 3- (naphthalen-1-yl) aniline (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, thereby obtaining intermediate 194a. (yield: 86%)
2. Synthesis of Compound 194
Intermediate 194a (1.0 eq.) 2- (4 '-bromo- [1,1' -biphenyl)]-3-yl) naphthalene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 194 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 663.2562; measurement value: 663.2559 )
Synthesis example 20: synthesis of Compound 207
1. Synthesis of intermediate 207a
3-bromo-9, 9-dimethyl-9H-fluorene (1.1 eq), 4- (naphthalen-2-yl) aniline (1.0 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolvedThe reaction mixture was obtained by dissolving in toluene and stirring at 80℃under nitrogen atmosphere for 2 hours. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby intermediate 207a was obtained. (yield: 86%)
2. Synthesis of Compound 207
Intermediate 207a (1.0 eq.) 2- (4 '-bromo- [1,1' -biphenyl)]-3-yl) naphthalene (1.1 eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene and stirred at 80 ℃ under nitrogen atmosphere for 2 hours to obtain a reaction mixture. After cooling the reaction mixture, it was subjected to three extraction processes each by using ethyl acetate and water, and first by using MgSO 4 The organic layer thus obtained was dried, and then dried again under reduced pressure. The resultant product was subjected to column chromatography, whereby compound 207 was obtained. ( Yield: 86%, HRMS (ESI): calculated values: 689.3083; measurement value: 689.3090 )
The synthesis methods of compounds other than the compounds synthesized in the synthesis examples can be easily recognized by those skilled in the art by referring to the synthesis routes and the starting materials.
Comparative example 1
As an anode, 15. OMEGA/cm was used 2 The ITO glass substrate (product of Corning Co., ltd.) was cut into dimensions of 50 mm. Times.50 mm. Times.0.7 mm, sonicated in isopropyl alcohol and pure water in each solvent for 5 minutes, and cleaned by irradiating ultraviolet rays thereto and exposing it to ozone for 30 minutes, and loaded onto a vacuum deposition apparatus.
N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]-4,4' -diamine (hereinafter HIL 1) is vacuum deposited on the anode to form a film having the following propertiesAnd vacuum depositing a compound 103 on the hole injection layer to form a hole injection layer having +.>Is a hole transport layer of thickness
2- (10-Phenylanthracen-9-yl) dibenzo [ b, d ] as a host]Furan (hereinafter referred to as host 1) and 5, 9-bis (4- (tert-butyl) phenyl) -7-methyl-5, 9-dihydro-5, 9-diaza-13 b-boronaphtho [3,2,1-de ] as dopants]Anthracene (hereinafter referred to as dopant 1) was co-deposited on the hole transport layer at a weight ratio of 98:2 to form a film havingIs a layer of a thickness of the emissive layer.
Alq is to 3 Vacuum deposition on the emissive layer to form a film havingElectron transport layer of a thickness of (a). Vacuum depositing LiF as alkali metal halide on the electron transport layer to form a film having +.>Electron injection layer of the thickness of (2), and vacuum depositing Al thereon to form a film having +.>Thereby forming LiF/Al electrodes, thereby completing the fabrication of the light emitting device.
Comparative example 2
A light-emitting device was manufactured in substantially the same manner as in comparative example 1, except that two hole-transporting layers were formed by arranging the first hole-transporting layer and the second hole-transporting layer in this order from the anode using the compounds shown in table 1 when forming the hole-transporting layers.
Examples 1 to 4
Each light-emitting device was manufactured in substantially the same manner as in comparative example 1, except that when a hole-transporting layer was formed, three hole-transporting layers were formed by arranging the first hole-transporting layer, the second hole-transporting layer, and the third hole-transporting layer in this order from the anode using the compounds shown in table 1.
Examples 5 to 9
Each light-emitting device was manufactured in substantially the same manner as in comparative example 1, except that in forming the hole-transporting layer, four hole-transporting layers were formed by arranging the first hole-transporting layer, the second hole-transporting layer, the third hole-transporting layer, and the fourth hole-transporting layer in this order from the anode using the compounds shown in table 1.
Evaluation example 1 (evaluation of characteristics of light-emitting device)
In order to evaluate the characteristics of the light emitting devices of the above examples and comparative examples, the light emitting devices at 50mA/cm were measured by using the Keithley SMU 236 and the luminance meter PR650, respectively 2 Driving voltage (V) at current density, luminance (cd/m) 2 ) Light-emitting efficiency (cd/a), and half life, and the results thereof are shown in table 2. In Table 2, the half life is at 100mA/cm 2 A measure of the time (hr) it takes for the luminance to reach 50% of the initial luminance at the current density of (a).
TABLE 1
TABLE 2
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Referring to table 2, it was confirmed that the first compound was used as compared with the light-emitting devices of comparative examples 1 and 2; a second compound; and at least one of the third compound and the fourth compound as a hole transporting material the light emitting device of examples 1 to 9 has excellent characteristics in terms of driving voltage, luminance, light emitting efficiency, and/or half life.
According to the embodiment, the light emitting device has a low driving voltage, high light emitting efficiency, and long life.
Embodiments have been disclosed herein and, although terminology is employed, they are used and interpreted in a generic and descriptive sense only and not for purpose of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and/or elements described with reference to an embodiment may be used alone or in combination with features, characteristics, and/or elements described with reference to other embodiments unless specifically indicated otherwise. Accordingly, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as set forth in the following claims.
Claims (20)
1. A light emitting device, comprising:
a first electrode;
a second electrode facing the first electrode;
an interlayer between the first electrode and the second electrode and comprising an emissive layer;
a first compound represented by formula 1;
a second compound represented by formula 2; and
at least one of a third compound represented by formula 3 and a fourth compound represented by formula 4, wherein the first compound to the fourth compound are different from each other:
[ 1]
[ 2]
[ 3]
[ 4]
Wherein, in the formulas 1 to 4,
L 11 to L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Each independently is a single bond, unsubstituted or substituted with at least one R 10a Substituted C 5 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, n11 to n14, n21 to n23, n31, n32, n41 and n42 are each independently integers selected from 1 to 3,
Ar 11 to Ar 14 、Ar 21 And Ar is a group 22 Each independently is not takenSubstituted or by at least one R 10a Substituted C 5 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
R 21 and R is 22 Each independently is unsubstituted or deuterated, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 1 -C 30 Alkyl or C 3 -C 30 A cycloalkyl group,
R 31 and R is 32 Each independently is unsubstituted or deuterium, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 3 -C 30 A cycloalkyl group,
CY 1 is a phenyl group or a naphthyl group,
CY 41 and CY 42 Each independently is C 5 -C 30 Carbocyclyl, an
T 3 And T 4 Each independently is a group represented by formula 5,
[ 5]
Wherein, in the formula 5,
t is C (X) 1 )(X 2 ) O, S or N (X) 1 )，
X 1 And X 2 Each independently being unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 30 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 5 -C 30 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 30 Heterocyclyl group, an
X 1 And X 2 Optionally linked to each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclyl or unsubstituted or substituted toLess than one R 10a Substituted C 1 -C 30 A heterocyclic group,
wherein, in the formulas 1 to 5,
R 11 、R 23 、R 41 、R 42 and RT is each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
a11 is an integer selected from 0 to 6,
a23 is an integer selected from 0 to 7,
a31 and a32 are each independently integers selected from 1 to 5,
a41 and a42 are each independently integers selected from 0 to 9,
at is an integer selected from 0 to 7,
* Indicating the binding site to the adjacent atom,
R 10a the method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or any combination thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or any combination thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) Or (b)
-P(＝O)(Q 31 )(Q 32 ) And (2) and
Q 1 to Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
2. The light-emitting device of claim 1, wherein,
the first electrode is an anode and the second electrode is an anode,
the second electrode is a cathode electrode and,
the interlayer further comprises:
a hole transport region between the emissive layer and the first electrode; and
an electron transport region between the emissive layer and the second electrode,
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
3. The light-emitting device according to claim 2, wherein,
the hole transport region includes at least one of the hole injection layer, the hole transport layer, and the electron blocking layer, and
At least one of the hole injection layer, the hole transport layer, and the electron blocking layer includes:
the first compound;
the second compound; and
at least one of the third compound and the fourth compound.
4. The light-emitting device according to claim 2, wherein,
the hole transport region includes the hole transport layer,
the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer,
the first hole transport layer is between the first electrode and the second hole transport layer,
the first hole transport layer comprises the first compound,
the second hole transport layer is between the first hole transport layer and the third hole transport layer,
the second hole transport layer includes the second compound, and
the third hole transport layer includes at least one of the third compound and the fourth compound.
5. The light-emitting device according to claim 2, wherein,
the hole transport region includes the hole transport layer,
the hole transport layer comprises a first hole transport layer, a second hole transport layer, a third hole transport layer, and a fourth hole transport layer,
The first hole transport layer is between the first electrode and the second hole transport layer,
the first hole transport layer comprises the first compound,
the second hole transport layer is between the first hole transport layer and the third hole transport layer,
the second hole transport layer comprises the second compound,
the third hole transport layer is between the second hole transport layer and the fourth hole transport layer,
the third hole transport layer includes the third compound, and
the fourth hole transport layer includes the fourth compound.
6. The light emitting device according to claim 1, wherein in formulae 1 to 4,
L 11 to L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Each independently is:
a single bond; or (b)
Each unsubstituted or substituted by at least one R 10a Substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoboronpentadienyl, benzophospholanyl, indenyl, benzothiophenyl, benzogermanopyranenyl, benzothiophenyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoboronpentadienyl, dibenzophospholanyl, fluorenyl, dibenzosilol, dibenzogermanium heterocyclopentadienyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophen-5-oxide, 9H-fluoren-9-onyl, dibenzothiophen-5, 5-dioxide, azaindolyl, azabenzoboronpentadienyl, azaboronpentadienyl azabenzophospholanenyl, azaindenyl, azabenzothiophenyl, azabenzogermanium cyclopentenyl, azabenzothiophenyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azabenzoborolidienyl, azadibenzophospholanenyl, azafluorenyl, azadibenzosilolyl, azabenzogermanium heterocyclopenadienyl, azadibenzothiophenyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophen-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophen-5, 5-dioxide, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthroline, pyrrolyl, pyrazolyl Imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolinyl or 5,6,7, 8-tetrahydroquinolinyl, and
R 10a as defined in formulas 1 to 4.
7. The light emitting device according to claim 1, wherein in formulae 1 to 4,
L 11 to L 14 、L 21 To L 23 、L 31 、L 32 、L 41 And L 42 Each independently is a single bond or phenylene.
8. The light-emitting device according to claim 1, wherein in formula 1 and formula 2, ar 11 To Ar 14 、Ar 21 And Ar is a group 22 Each independently is:
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzooxazolyl, benzotriazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, dibenzothialoyl, benzofluorenyl, benzocarbazolyl, naphthazolyl, naphthacene Silol, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilol, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl or azadibenzosilol). Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilol, benzofluorenyl, benzocarbazolyl, naphtofuranyl, dinaphtalothienyl, dinaphtalosilol, indenocarbazolyl, indolocarbazolyl, benzocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or any combination thereof, and
Q 31 to Q 33 Each independently is:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
Each unsubstituted or deuterium-substituted, C 1 -C 20 An alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof, substituted with n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl.
9. The light-emitting device according to claim 1, wherein in formula 1 and formula 2, ar 11 To Ar 14 、Ar 21 And Ar is a group 22 Each independently is unsubstituted or deuterated, -F, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl or any combination thereof.
10. The light-emitting device according to claim 1, wherein in formula 2, R 21 And R is 22 Identical to each other.
11. The light-emitting device according to claim 1, wherein in formula 3, R 31 And R is 32 Each independently is unsubstituted or deuterated, -F, cyano, C 1 -C 10 Cyclopentyl, cyclohexyl, cycloheptyl substituted with alkyl or any combination thereofCyclooctyl, adamantyl, bicyclo [2.2.1 ]Heptyl, bicyclo [1.1.1]Amyl, bicyclo [2.1.1 ]]Hexyl or bicyclo [2.2.2]Octyl.
12. The light-emitting device according to claim 1, wherein in formula 4,
CY 41 and CY 42 Each is naphthyl, or
CY 41 And CY 42 One of which is naphthyl and CY 41 And CY 42 The other of which is phenyl or phenanthryl.
13. The light emitting device according to claim 1, wherein in formula 1, formula 2 and formula 4,
R 11 is hydrogen, deuterium or-F, and
R 23 、R 41 and R is 42 Each independently is:
hydrogen, deuterium or-F; or (b)
Unsubstituted or deuterium-F, cyano, C 1 -C 20 Alkyl groups or any combination thereof.
14. The light-emitting device according to claim 1, wherein in formula 5, X 1 And X 2 Each independently is:
c unsubstituted or substituted with deuterium, -F, cyano or any combination thereof 1 -C 10 An alkyl group; or (b)
Each unsubstituted or deuterium, -F, cyano, C 1 -C 10 C substituted by alkyl or any combination thereof 2 -C 10 Alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1]Heptyl, bicyclo [1.1.1]Amyl, bicyclo [2.1.1 ]]Hexyl, bicyclo [2.2.2]Octyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl.
15. The light-emitting device according to claim 1, wherein in formula 5,
When T is C (X 1 )(X 2 ) When X is 1 And X 2 Identical to each other.
16. The light-emitting device according to claim 1, wherein in formula 5, RT is:
hydrogen, deuterium, -F, or cyano; or (b)
Unsubstituted or deuterium-F, cyano, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy or any combination thereof 6 -C 10 Aryl groups.
17. The light emitting device of claim 1, wherein the emissive layer emits blue light having a maximum emission wavelength in the range of 430nm to 490 nm.
18. An electronic device comprising the light-emitting device according to any one of claims 1 to 17.
19. The electronic device of claim 18, further comprising a thin film transistor, wherein,
the thin film transistor includes a source electrode and a drain electrode, and
the first electrode of the light emitting device is electrically connected to the source electrode or the drain electrode.
20. The electronic device of claim 19, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2022-0016967 | 2022-02-09 | ||
| KR1020220063592A KR20230121523A (en) | 2022-02-09 | 2022-05-24 | Light emitting device and electronic apparatus including the light emitting device |
| KR10-2022-0063592 | 2022-05-24 |
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| Publication Number | Publication Date |
|---|---|
| CN116583161A true CN116583161A (en) | 2023-08-11 |
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| CN202310098840.5A Pending CN116583161A (en) | 2022-02-09 | 2023-02-08 | Light emitting device and electronic apparatus including the same |
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| CN (1) | CN116583161A (en) |
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