U.S. patent application number 14/534830 was filed with the patent office on 2015-03-19 for luminescence device and display apparatus.
The applicant listed for this patent is CANON KABUSHIKI KAISHA. Invention is credited to Manabu Furugori, Satoshi Igawa, Jun Kamatani, Seishi Miura, Takashi Moriyama, Koji Noguchi, Shinjiro Okada, Takao Takiguchi, Akira Tsuboyama.
Application Number | 20150076478 14/534830 |
Document ID | / |
Family ID | 27345317 |
Filed Date | 2015-03-19 |
United States Patent
Application |
20150076478 |
Kind Code |
A1 |
Kamatani; Jun ; et
al. |
March 19, 2015 |
LUMINESCENCE DEVICE AND DISPLAY APPARATUS
Abstract
A metal coordination compound represented by any one of formulas
(1)-(5). An organic luminescence device including an anode, a
cathode, and an organic layer, which contains the metal
coordination compound, disposed between the anode and the
cathode.
Inventors: |
Kamatani; Jun;
(Kawasaki-shi, JP) ; Okada; Shinjiro;
(Isehara-shi, JP) ; Tsuboyama; Akira;
(Sagamihara-shi, JP) ; Takiguchi; Takao; (Tokyo,
JP) ; Miura; Seishi; (Sagamihara-shi, JP) ;
Noguchi; Koji; (Sagamihara-shi, JP) ; Moriyama;
Takashi; (Kawasaki-shi, JP) ; Igawa; Satoshi;
(Fujisawa-shi, JP) ; Furugori; Manabu;
(Atsugi-shi, JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
CANON KABUSHIKI KAISHA |
Tokyo |
|
JP |
|
|
Family ID: |
27345317 |
Appl. No.: |
14/534830 |
Filed: |
November 6, 2014 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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12371104 |
Feb 13, 2009 |
8920943 |
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14534830 |
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11694754 |
Mar 30, 2007 |
7527879 |
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12371104 |
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11329181 |
Jan 11, 2006 |
7544426 |
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11694754 |
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10073012 |
Feb 12, 2002 |
7147935 |
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11329181 |
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PCT/JP01/10487 |
Nov 30, 2001 |
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10073012 |
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Current U.S.
Class: |
257/40 ;
546/4 |
Current CPC
Class: |
C09K 2211/1044 20130101;
C09K 11/06 20130101; C09K 2211/1029 20130101; H01L 51/005 20130101;
C07F 15/0093 20130101; C09K 2211/1033 20130101; H01L 51/0085
20130101; H05B 33/14 20130101; C09K 2211/1092 20130101; C09K
2211/1007 20130101; C07F 15/004 20130101; C09K 2211/1048 20130101;
C09K 2211/1011 20130101; C07F 15/008 20130101; H01L 27/3244
20130101; H01L 51/5016 20130101; H01L 51/5012 20130101; H01L
51/0059 20130101; C09K 2211/185 20130101; Y10S 428/917 20130101;
C09K 2211/1037 20130101; H01L 51/0081 20130101; C09K 2211/1051
20130101; H01L 51/0084 20130101; H01L 51/5234 20130101; C07F
15/0066 20130101 |
Class at
Publication: |
257/40 ;
546/4 |
International
Class: |
H01L 51/00 20060101
H01L051/00; H01L 27/32 20060101 H01L027/32; H01L 51/52 20060101
H01L051/52; H01L 51/50 20060101 H01L051/50 |
Foreign Application Data
Date |
Code |
Application Number |
Nov 30, 2000 |
JP |
2000-364650 |
Mar 8, 2001 |
JP |
2001-064205 |
Apr 26, 2001 |
JP |
2001-128928 |
Claims
1-3. (canceled)
4. A light emitting compound represented by formula: ##STR00073##
wherein R.sub.1 is CH.sub.3, C.sub.2H.sub.5, or a normal alkyl
group having 3-8 carbon atoms; and each R.sub.2 is, independently,
H or CH.sub.3.
5. The light emitting compound according to claim 4, represented by
any one of formulas (1) to (6): ##STR00074## ##STR00075##
6. The light emitting compound according to claim 4, wherein said
light emitting compound emits red.
7. The light emitting compound according to claim 5, wherein said
light emitting compound emits red.
8. An organic luminescence device comprising: an anode and a
cathode; and an organic layer disposed between the anode and the
cathode, wherein the organic layer comprises a light emitting
compound according to claim 4.
9. A picture display apparatus comprising: an organic luminescence
device according to claim 8 and means for supplying an electric
signal to the organic luminescence device.
10. The light emitting compound according to claim 4, wherein the
normal alkyl group having 3-8 carbon atoms is any one of
n-C.sub.4H.sub.9, n-C.sub.6H.sub.13, and n-C.sub.8H.sub.17.
11. An active matrix display comprising an organic luminescence
device according to claim 8.
12. The active matrix display according to claim 11, further
comprising: a gate selection line; an information signal line; and
a switching element, wherein the switching element is connected
with the organic luminescence device.
13. An illumination apparatus comprising an organic luminescence
device according to claim 8.
14. A printer comprising: a light source, wherein the light source
includes an organic luminescence device according to claim 8.
15. The organic luminescence device according to claim 8, further
comprising a heterocompound disposed between the anode and the
cathode, wherein the heterocompound is at least one of CBP, BPhen,
BCP, Alq3, and Balq.
16. An organic luminescence apparatus comprising: an alkali-free
transparent substrate; and an organic luminescence device according
to claim 8.
17. An organic luminescence apparatus comprising: a transparent
substrate; and an organic luminescence device according to claim 8,
wherein the organic luminescence device includes a transparent
electrode, and wherein the transparent electrode is one of the
anode and the cathode that is closest to the transparent
substrate.
18. An organic luminescence apparatus comprising: a transparent
substrate; and an organic luminescence device according to claim 8,
wherein light emitted from the organic luminescence device passes
through the transparent substrate.
19. The organic luminescence device according to claim 8, wherein
the organic layer is a light emitting layer which emits a light
having a red color.
Description
[0001] This application is a division of Ser. No. 11/694,754, filed
Mar. 30, 2007, which is a division of Ser. No. 11/329,181, filed
Jan. 11, 2006, which is a division of application Ser. No.
10/073,012, filed Feb. 12, 2002, now U.S. Pat. No. 7,147,935, which
is a continuation of International Application PCT/JP01/10487,
filed Nov. 30, 2001. All prior applications are incorporated herein
by reference.
TECHNICAL FIELD
[0002] The present invention relates to an organic luminescence
device (also called an organic electroluminescence device or an
organic EL device) for use in a planar light source, a planar
display, and the like. Particularly, the present invention relates
to a novel metal coordination compound and a luminescence device
having a high luminescence efficiency and undergoing little change
with time by using a metal coordination compound of a specific
structure.
BACKGROUND ART
[0003] An example of a conventional organic luminescence device is
e.g., one using luminescence of a vacuum-deposited anthracene film
(Thin Solid Films, 94 (1982) 171). Recently, however, in view of
the advantages, such as ease of providing a large-area device
compared with an inorganic luminescence device, and a possibility
of realizing desired luminescence colors due to the development of
various new materials and drivability at low voltages, extensive
studies thereof for the production of high-speed responsive and
high efficiency luminescence devices have been conducted.
[0004] As precisely described in Macromol. Symp. 125, 1-48 (1997),
for example, an organic EL device generally has an organization
comprising a pair of upper and lower electrodes formed on a
transparent substrate, and organic material layers including a
luminescence layer disposed between the electrodes.
[0005] In the luminescence layer, aluminum quinolinol complexes
(inclusive of Alq3 shown hereinafter as a representative example)
having an electron-transporting characteristic and a luminescence
characteristic, are used for example. In a hole-transporting layer,
a material having an electron-donative property, such as a
triphenyldiamine derivative (inclusive of .alpha.-NPD shown
hereinafter as a representative example), is used for example.
[0006] Such a device shows a current-rectifying characteristic such
that when an electric field is applied between the electrodes,
holes are injected from the anode and electrons are injected from
the cathode.
[0007] The injected holes and electrons are recombined in the
luminescence layer to form excitons, which emit luminescence when
they are transitioned to the ground state.
[0008] In this process, the excited states include a singlet state
and a triplet state and a transition from the former to the ground
state is called fluorescence and a transition from the latter is
called phosphorescence. Materials in theses states are called
singlet excitons and triplet excitons, respectively.
[0009] In most of the organic luminescence devices studied
heretofore, fluorescence caused by the transition of a singlet
exciton to the ground state, has been utilized. On the other hand,
in recent years, devices utilizing phosphorescence via triplet
excitons have been studied.
[0010] Representative published literature may include: [0011]
Article 1: Improved energy transfer in electrophosphorescent device
(D. F. O'Brien, et al., Applied Physics Letters, Vol. 74, No. 3, p.
422 (1999)); and [0012] Article 2: Very high-efficiency green
organic light-emitting devices based on electrophosphorescence (M.
A. Baldo, et al., Applied Physics Letters, Vol. 75, No. 1, p. 4
(1999)).
[0013] In these articles, a structure including four organic layers
sandwiched between the electrodes, and the materials used therein
include carrier-transporting materials and phosphorescent
materials, of which the names and structures are shown below
together with their abbreviations.
[0014] Alq3: aluminum quinolinol complex
[0015] .alpha.-NPD:
N4,N4'-di-naphthalene-1-yl-N4,N4'-diphenyl-biphenyl-4,4'-diamine
[0016] CBP: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
[0017] PtOEP: platinum-octaethylporphyrin complex
[0018] Ir(ppy).sub.3: iridium-phenylpyridine complex
##STR00001##
[0019] The above-mentioned Articles 1 and 2 both have reported
structures, as exhibiting a high efficiency, including a
hole-transporting layer comprising .alpha.-NPD, an
electron-transporting layer comprising Alq3, an exciton
diffusion-preventing layer comprising BCP, and a luminescence layer
comprising CBP as a host and ca. 6% of PtOEP or Ir(ppy).sub.3 as a
phosphorescent material dispersed in mixture therein.
[0020] Such a phosphorescent material is particularly noted at
present because it is expected to provide a high luminescence
efficiency in principle for the following reasons. More
specifically, excitons formed by carrier recombination comprise
singlet excitons and triplet excitons in a probability ratio of
1:3. Conventional organic EL devices have utilized fluorescence of
which the luminescence efficiency is limited to at most 25%. On the
other hand, if phosphorescence generated from triplet excitons is
utilized, an efficiency of at least three times is expected, and
even an efficiency of 100%, i.e., four times, can be expected in
principle, if a transition owing to intersystem crossing from a
singlet state having a higher energy to a triplet state is taken
into account.
[0021] However, like a fluorescent-type device, such an organic
luminescence device utilizing phosphorescence is generally required
to be further improved regarding the deterioration of luminescence
efficiency and device stability.
[0022] The reason of the deterioration has not been fully
clarified, but the present inventors consider as follows based on
the mechanism of phosphorescence.
[0023] In the case where the luminescence layer comprises a host
material having a carrier-transporting function and a
phosphorescent guest material, a process of phosphorescence via
triplet excitons may include unit processes as follows:
[0024] 1. transportation of electrons and holes within a
luminescence layer,
[0025] 2. formation of host excitons;
[0026] 3. excitation energy transfer between host molecules,
[0027] 4. excitation energy transfer from the host to the
guest,
[0028] 5. formation of guest triplet excitons, and
[0029] 6. transition of the guest triplet excitons to the ground
state and phosphorescence.
[0030] Desirable energy transfer in each unit process and
luminescence are caused in competition with various energy
deactivation processes.
[0031] Needless to say, a luminescence efficiency of an organic
luminescence device is increased by increasing the luminescence
quantum yield of a luminescence center material.
[0032] Particularly, in a phosphorescent material, this may be
attributable to a life of the triplet excitons which is longer by
three or more digits than the life of a singlet exciton. More
specifically, because it is held in a high-energy excited state for
a longer period, it is liable to react with surrounding materials
and cause polymer formation among the excitons, thus incurring a
higher probability of deactivation process resulting in a material
change or life deterioration.
[0033] Further, in view of the formation of a full-color display
device, luminescence materials providing luminescence colors which
are as close as possible to pure three primary colors of blue,
green and red, are desired, but there have been few luminescence
materials giving a luminescence, color of pure red, so that the
realization of a good full-color display device has been
restricted.
DISCLOSURE OF INVENTION
[0034] Accordingly, a principal object of the present invention is
to provide a compound capable of high efficiency luminescence and
showing a high stability as a luminescent material for use in a
Phosphorescent luminescence device. Particularly, it is an object
to provide a luminescence material compound which is less liable to
cause energy deactivation in a long life of excited energy state
and is also chemically stable, thus providing a longer device life.
A further object of the present invention is to provide a red
luminescence material compound capable of emitting pure red
suitable for forming a full-color display device.
[0035] Inclusively, principal objects of the present invention are
to provide a luminescence material which exhibits a high
luminescence efficiency, retains a high luminance for a long period
and is capable of red luminescence based on phosphorescent
luminescence materials, and also provide a luminescence device and
a display apparatus using the same.
[0036] In the present invention, a metal complex is used as a
luminescence material, particularly a novel luminescent metal
complex compound comprising iridium as a center metal and an
isoquinolyl group as a ligand.
[0037] More specifically, the present invention uses as a
luminescence material a metal coordination compound having at least
one partial structure represented by formula (1) below:
ML (1),
wherein the partial structure ML is represented by formula (2)
below:
##STR00002##
wherein M is a metal atom of Ir, Pt, Rh or Pd; N and C are nitrogen
and carbon atoms, respectively; A is a cyclic group capable of
having a substituent, including the carbon atom and bonded to the
metal atom M via the carbon atom; B is an isoquinolyl group capable
of having a substituent, including the nitrogen atom and bonded to
the metal atom M via the nitrogen atom, with the proviso that one
or two of CH groups forming the isoquinolyl group can be replaced
with a nitrogen atom and the cyclic group A is coordination-bonded
to a position-1 carbon atom of the isoquinolyl group.
[0038] More specifically, the present invention uses a metal
coordination compound having an entire structure represented by
formula (3) below:
ML.sub.mL'.sub.n (3),
wherein M is a metal atom of Ir, Pt, Rh or Pd; L and L' are
mutually different bidentate ligands; m is 1, 2 or 3, and n is 0, 1
or 2 with the proviso that m+n is 0.2 or 3; a partial structure
ML'.sub.n is represented by formula (4), (5) or (6) shown
below:
##STR00003##
[0039] The present invention also uses as a luminescence material,
a metal coordination compound which is entirely represented by
formula (7) below:
##STR00004##
wherein Cl denotes a chlorine atom, M' denotes iridium Ir or
rhodium Rh, and m' is 2.
[0040] The present invention also provides high-performance organic
luminescence device and display apparatus using the above-mentioned
novel metal coordination compound as an organic luminescence
material.
[0041] Preferred embodiments of the present invention include the
following:
[0042] A metal coordination compound, wherein n is 0 in the above
formula (3).
[0043] A metal coordination compound, wherein the cyclic groups A
and A' are independently selected from phenyl group, naphthyl
group, thienyl group, fluorenyl group, thianaphthyl group,
acenaphthyl group, anthranyl group, phenanthrenyl group, pyrenyl
group, or carbazolyl group, as an aromatic cyclic group capable of
having a substituent with the proviso that the aromatic cyclic
group can include one or two CH groups that can be replaced with a
nitrogen atom.
[0044] A metal coordination compound, wherein the cyclic groups A
and A' are selected from phenyl group, 2-naphthyl group, 2-thienyl
group, 2-fluorenyl group, 2-thianaphthyl group, 2-anthranyl group,
2-phenanthrenyl group, 2-pyrenyl group, or 3-carbazolyl group, as
an aromatic cyclic group capable of having a substituent with the
proviso that the aromatic cyclic group can include one or two CH
groups that can be replaced with a nitrogen atom.
[0045] A metal coordination compound, wherein the aromatic cyclic
group is phenyl group capable of having a substituent.
[0046] A metal coordination compound, wherein a hydrogen atom is
attached to a position-6 carbon atom of the phenyl group capable of
having a substituent next to a position-1 carbon atom bonded to the
cyclic group B.
[0047] A metal coordination compound, wherein the cyclic groups 8'
and B'' are independently selected from isoquinolyl group, quinolyl
group, 2-azaanthranyl group, phenanthridinyl group, pyridyl group,
oxazolyl group, thiazolyl group, bensoxazolyl group, or
benzthiazolyl group, as an aromatic cyclic group capable of having
a substituent with the proviso that the aromatic cyclic group can
include one or two CH groups that can be replaced with a nitrogen
atom.
[0048] A metal coordination compound, wherein the cyclic groups B'
and B'' are selected from isoquinolyl group or pyridyl group, as an
aromatic cyclic group capable of having a substituent with the
proviso that the aromatic cyclic group can include one or two CH
groups that can be replaced with a nitrogen atom.
[0049] A metal coordination compound, wherein the cyclic group B'
in the formula (4) is isoquinolyl group capable of having a
substituent.
[0050] A metal coordination compound, wherein the cyclic groups A,
A', B, B' and B'' are independently non-substituted, or have a
substituent selected from a halogen atom or a linear or branched
alkyl group having 1 to 20 carbon atoms {of which the alkyl group
can include one or non-neighboring two or more methylene groups
that can be replaced with --O--, --S--, --CO--, --CO--O--,
--O--CO--, --CH.dbd.CH--, --C.ident.C--, or a divalent aromatic
group capable of having a substituent (that is a halogen atom, or a
linear or branched alkyl group having 1 to 20 carbon atoms (of
which the alkyl group can include one or non-neighboring two or
more methylene groups that can be replaced with --O--, and the
alkyl group can include a hydrogen atom that can be optionally
replaced with a fluorine atom)), and the alkyl group can include a
hydrogen atom that can be optionally replaced with a fluorine
atom).
[0051] A metal coordination compound, wherein the cyclic group A in
the formula (7) is selected from phenyl group, naphthyl group,
thienyl group, fluorenyl group, thianaphthyl group, acenaphthyl
group, anthranyl group, phenanthrenyl group, pyrenyl group, or
carbazolyl group, as an aromatic cyclic group capable of having a
substituent with the proviso that the aromatic cyclic group can
include one or two CH groups that can be replaced with a nitrogen
atom.
[0052] A metal coordination compound, wherein the aromatic cyclic
group is selected from phenyl group, 2-naphthyl group, 2-thienyl
group, 2-fluorenyl group, 2-thianaphthyl group, 2-anthranyl group,
2-phenanthrenyl group, 2-pyrenyl group or 3-carbazolyl group, each
capable of having a substituent with the proviso that the aromatic
cyclic group can include one or two CH groups that can be replaced
with a nitrogen atom.
[0053] A metal coordination compound, wherein the aromatic cyclic
group is phenyl group capable of having a substituent.
[0054] A metal coordination compound, wherein a hydrogen atom is
attached to a position-6 carbon atom of the phenyl group capable of
having a substituent next to a position-1 carbon atom bonded to the
cyclic group B.
[0055] A metal coordination compound, wherein the cyclic groups A
and B in the formula (7) are independently non-substituted, or have
a substituent selected from a halogen atom or a linear or branched
alkyl group having 1 to 20 carbon atoms (of which the alkyl group
can include one or non-neighboring two or more methylene groups
that can be replaced with --O--, --S--, --CO--, --CO--O--,
--O--CO--, --CH.dbd.CH--, --C.ident.C--, or a divalent aromatic
group capable of having a substituent (that is a halogen atom, a
cyano atom, a nitro atom, a trialkylsilyl group (of which the alkyl
groups are independently a linear or branched alkyl group), a
linear or branched alkyl group having 1 to 20 carbon atoms (of
which the alkyl group can include one or non-neighboring two or
more methylene groups that can be replaced with --O--, and the
alkyl group can include a hydrogen atom that can be optionally
replaced with a fluorine atom)), and the alkyl group can include a
hydrogen atom that can be optionally replaced with a fluorine
atom}.
[0056] A metal coordination compound, wherein M in the formula (1)
is iridium.
[0057] A metal coordination compound, wherein M in the formula (7)
is iridium.
[0058] A metal coordination compound, having a partial structure ML
represented by the formula (2) and represented by formula (8)
below:
Ir[Rp-Ph-IsoQ-R'q].sub.3 (8),
wherein Ir is iridium; partial structure Ph-IsoQ denotes
1-phenylisoquinolyl group; substituents R and R' are selected from
hydrogen, fluorine or a linear or branched alkyl group represented
by C.sub.nH.sub.2n+1 (wherein H can be replaced with F, a
non-adjacent methylene group can be replaced with oxygen and n is
an integer of 1 to 20), p and q are integers of at least 1
representing numbers of the substituents R and R' bonded to the
phenyl group and the isoquinolyl group, respectively, wherein a
position-2 carbon atom of the phenyl group and a nitrogen atom of
IsoQ are coordination-bonded to Ir.
[0059] A metal coordination compound, wherein the partial structure
Rp-Ph is 4-alkylphenyl group in the formula (8), and the
substituent R' is hydrogen.
[0060] A metal coordination compound, wherein in the formula (8),
the substituent R is hydrogen, and R'q represents a fluoro or
trifluoromethyl group substituted at a 4- or 5-position.
[0061] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is 5-fluorophenyl group, and R'q is a
hydrogen atom or a fluorine atom or trifluoromethyl group
substituted at a 4- or 5-position.
[0062] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is 4-fluorophenyl group, and R'q is a
hydrogen atom or a fluorine atom or trifluoromethyl group
substituted at a 4- or 5-position.
[0063] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is 3,5-difluorophenyl group, and R'q
is a hydrogen atom or fluorine atom or trifluoromethyl group
substituted at a 4- or 5-position.
[0064] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is 3,4,5-trifluorophenyl group, and
R'q is a hydrogen atom or a fluorine atom or trifluoromethyl group
substituted at a 4- or 5-position.
[0065] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is 4-trifluoromethylphenyl group, and
R'q is a hydrogen atom or a fluorine atom or trifluoromethyl group
substituted at a 4- or 5-position.
[0066] A metal coordination compound, wherein in the formula (8),
the partial structure .English Pound.p-Ph- is
5-trifluoromethylphenyl group, and R'q is a hydrogen atom or a
fluorine atom or trifluoromethyl group substituted at a 4- or
5-position.
[0067] A metal coordination compound, wherein in the formula (8),
the structure Rp-Ph is a 1-(3,4,5,6-tetrafluorophenyl) group, and
in R'q is 1 or 6 and R' is a hydrogen atom, a trifluoromethyl group
substituted at a 4- or 5-position or such that IsoQ-R'q is a
3,4,5,6,7,8-hexafluoroisoquinoline group.
[0068] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is 4-alkylphenyl group (wherein the
alkyl group is a linear or branched alkyl group having 1 to 6
carbon atoms), and R'g is hydrogen.
[0069] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is 4-alkoxyphenyl group (wherein the
alkoxy group is a linear or branched alkoxy group having 1 to 6
carbon atoms), and R'q is hydrogen.
[0070] A metal coordination compound, wherein in the formula (8),
the partial structure Rp-Ph- is a 4-trifluoromethyloxyphenyl group,
and R'q is a hydrogen or fluoro group or trifluoromethyl group
substituted at a 4- or 5-position.
[0071] A metal coordination compound, which is represented by the
formula (3) and is also represented by formula (9) below:
IrL.sub.mL'.sub.n (9),
wherein Ir represents iridium.
[0072] A metal coordination compound, represented by the formula
(9), wherein L.sub.m is represented by a formula of
[4-alkylphenylisoquinoline].sub.2 (wherein the alkyl group is
represented by C.sub.nH.sub.2n+1 and n is an integer of 1 to 8),
and L'.sub.n is 1-phenylisoquinoline.
[0073] A metal coordination compound, represented by the formula
(9), wherein L.sub.m is represented by a formula
[1-phenylisoquinoline].sub.2, and L'.sub.n is
4-alkylphenylisoquinoline (wherein the alkyl group has 1 to 8
carbon atoms).
[0074] A metal coordination compound, wherein one or two CH groups
in the isoquinolyl group capable of having a substituent in the
formula (1) are replaced with a nitrogen atom.
[0075] A metal coordination compound, wherein one or two CH groups
in the isoquinolyl group capable of having a substituent in the
formula (7) are replaced with a nitrogen atom.
[0076] An organic luminescence device, comprising: a pair of
electrodes disposed on a substrate, and a luminescence unit
comprising at least one organic compound disposed between the
electrodes, wherein the organic compound comprises a metal
coordination compound having at least one partial structure
represented by the formula (1) in claim 1.
[0077] An organic luminescence device, wherein the organic compound
comprises a metal coordination compound having a structure
represented by the formula (3).
[0078] An organic luminescence device, wherein the organic compound
comprises a metal coordination compound having a structure
represented by the formula (8).
[0079] An organic luminescence device, wherein the organic compound
comprises a metal coordination compound having a structure
represented by the formula (9).
[0080] An organic luminescence device, wherein a voltage is applied
between the electrodes to emit phosphorescence.
[0081] An organic luminescence device, wherein the phosphorescence
is red in luminescence color.
[0082] A picture display apparatus, comprising the above-mentioned
organic luminescence device, and a means for supplying electric
signals to the organic luminescence device.
BRIEF DESCRIPTION OF THE DRAWINGS
[0083] FIG. 1 illustrates embodiments of the luminescence device
according to the present invention.
[0084] FIG. 2 illustrates a simple matrix-type organic EL device
according to Example 8.
[0085] FIG. 3 illustrates drive signals used in Example 8.
[0086] FIG. 4 schematically illustrates a panel structure including
an EL device and drive means.
[0087] FIG. 5 is a graph showing voltage-efficiency luminance
characteristics of a device of Example 27.
[0088] FIG. 6 is a graph showing external Quantum efficiency of a
device of Example 27.
[0089] FIG. 7 shows a .sup.1H-NMR spectrum of a solution in heavy
chloroform of 1-phenylisoquinoline.
[0090] FIG. 8 shows a .sup.1H-NMR spectrum of a solution in heavy
chloroform of tris(1-phenylisoquinoline-C.sup.2,N)iridium
(III).
[0091] FIG. 9 shows a .sup.1H-NMR spectrum of a solution in heavy
chloroform of 1-(4-methylphenyl)-isoquinoline.
[0092] FIG. 10 shows a .sup.1H-NMR spectrum of a solution in heavy
chloroform of
tetrakis[1-4-methylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)-diiridiu-
m (III).
[0093] FIG. 11 shows a .sup.1H-NMR spectrum of a solution in heavy
chloroform of
bis[1-(4-methylphenyl)isoquinoline-C.sup.2,N](acetylacetonato)-iridium
(III).
[0094] FIG. 12 shows a .sup.1H-NMR spectrum of a solution in heavy
chloroform of tris[1-(4-methylphenyl)isoquinoline-C.sup.2,N]iridium
(III).
[0095] FIG. 13 shows a .sup.1H-NMR spectrum of a solution in heavy
chloroform of
bis[1-(4-n-octylphenyl)isoquinoline-C.sup.2,N](acetylacetonato)-iridium
(III).
BEST MODE FOR PRACTICING THE INVENTION
[0096] Basic structures of organic EL devices formed according to
the present invention are illustrated in FIGS. 1(a), (b) and
(c).
[0097] As shown in FIG. 1, an organic luminescence device generally
comprises, on a transparent electrode 15, a 50 to 200 nm-thick
transparent electrode 14, a plurality of organic film layers and a
metal electrode 11 formed so as to sandwich the organic layers.
[0098] FIG. 1(a) shows an embodiment wherein the organic
luminescence device comprises a luminescence layer 12 and a
hole-transporting layer 13. The transparent electrode 14 may
comprise ITO, etc., having a large work function so as to
facilitate hole injection from the transparent electrode 14 to the
hole-transporting layer 13. The metal electrode 11 comprises a
metal material having a small work function, such as aluminum,
magnesium or alloys of these elements, so as to facilitate electron
injection into the organic luminescence device.
[0099] The luminescence layer 12 comprises a compound according to
the present invention. The hole-transporting layer 13 may comprise,
e.g., a triphenyldiamine derivative, as represented by .alpha.-NPD
mentioned above, and also a material having an electron-donative
property as desired.
[0100] A device organized above exhibits a current-rectifying
characteristic, and when an electric field is applied between the
metal electrode 11 as a cathode and the transparent electrode 14 as
an anode, electrons are injected from the metal electrode 11 into
the luminescence layer 12, and holes are injected from the
transparent electrode 15. The injected holes and electrons are
recombined in the luminescence layer 12 to form excitons, which
cause luminescence. In this instance, the hole-transporting layer
13 functions as an electron-blocking layer to increase the
recombination efficiency at the boundary between the luminescence
layer 12 and the hole-transporting layer 13, thereby providing an
enhanced luminescence efficiency.
[0101] Further, in the structure of FIG. 1(b), an
electron-transporting layer 16 is disposed between the metal
electrode 11 and the luminescence layer 12 in FIG. 1(a). As a
result, the luminescence function is separated from the functions
of electron transportation and hole transportation to provide a
structure exhibiting more effective carrier blocking, thus
increasing the luminescence efficiency. The electron-transporting
layer 16, may comprise, e.g., an oxadiazole derivative.
[0102] FIG. 1(c) shows another desirable form of a four-layer
structure, including a hole-transporting layer 13, a luminescence
layer 12, an exciton diffusion prevention layer 17 and an
electron-transporting layer 16, successively from the side of the
transparent electrode 14 as the anode.
[0103] The luminescence materials used in the present invention are
most suitably metal coordination compounds represented by the
above-mentioned formulae (1) to (9), which are found to cause
high-efficiency luminescence in a red region around 600 mn, retain
high luminance for a long period and show little deterioration by
current passage.
[0104] The metal coordination compound used in the present
invention emits phosphorescence, and its lowest excited state is
believed to be an MLCT* (metal-to-ligand charge transfer) excited
state or .pi.-.pi.* excited state in a triplet state, and
phosphorescence is caused at the time of transition from such a
state to the ground state.
<<Measurement Methods>>
[0105] Hereinbelow, methods for measurement of some properties and
physical values described herein for characterizing the
luminescence material of the present invention will be
described.
[0106] (1) Judgment between phosphorescence and fluorescence
[0107] The identification of phosphorescence was effected depending
on whether deactivation with oxygen was caused or not. A solution
of a sample compound in chloroform after aeration with oxygen or
with nitrogen is subjected to photoillumination to cause
photo-luminescence. The luminescence is judged to be
phosphorescence if almost no luminescence attributable to the
compound is observed with respect to the solution aerated with
oxygen but photo-luminescence is confirmed with respect to the
solution aerated with nitrogen. In contrast thereto, in the case of
fluorescence, luminescence attributable to the compound does not
disappear even with respect to the solution aerated with oxygen.
The phosphorescence of all the compounds of the present invention
has been confirmed by this method unless otherwise noted
specifically.
[0108] (2) Phosphorescence yield (a relative quantum yield, i.e., a
ratio of an objective sample's quantum yield .PHI.(sample) to a
standard sample's quantum yield .PHI.(st)) is determined according
to the following formula:
.PHI.(sample)/.PHI.(st)=[Sem(sample)/Iabs(sample)]/[Sem(st)/Iabs(st)],
wherein Iabs(st) denotes an absorption coefficient at an excitation
wavelength of the standard sample; Sem(st), a luminescence spectral
areal intensity when excited at the same wavelength: Iabs(sample),
an absorption coefficient at an excitation wavelength of an
objective compound; and Sem(sample), a luminescence spectral areal
intensity when excited at the same wavelength.
[0109] Phosphorescence yield values described herein are relative
values with respect a phosphorescence yield .PHI.=1 of
Ir(ppy).sub.3 as a standard sample.
[0110] (3) A method of measurement of phosphorescence life is as
follows.
[0111] A sample compound is dissolved in chloroform and spin-coated
onto a quartz substrate in a thickness of ca. 0.1 .mu.m and is
exposed to pulsative nitrogen laser light at an excitation
wavelength of 337 nm at room temperature by using a luminescence
life meter (made by Hamamatsu Photonics K.K.). After completion of
the excitation pulses, the decay characteristic of luminescence
intensity is measured.
[0112] When an initial luminescence intensity is denoted by
I.sub.0, a luminescence intensity after t(sec) is expressed
according to the following formula with reference to a luminescence
life t(sec):
I=I.sub.0exp(-t/.tau.).
[0113] Thus, the luminescence life .tau. is a time period in which
the luminescence intensity I is attenuated down to 1/e of the
initial intensity I (I/I.sub.0=e.sup.-1, e is a base of natural
logarithm). A luminescence life of 80 nsec or longer, particularly
100 nsec or longer, is a second condition to be judged as
phosphorescence, whereas fluorescence shows a shorter luminescence
life on the order of several tens nsec or shorter.
[0114] The luminescence material exhibited high phosphorescence
quantum yields of 0.15 to 0.9 and short phosphorescence lives of
0.1 to 10 .mu.sec. A short phosphorescence life becomes a condition
for causing little energy deactivation and exhibiting an enhanced
luminescence efficiency. More specifically if the phosphorescence
life is long, the number of triplet state molecules maintained for
luminescence is increased, and the deactivation process is liable
to occur, thus resulting in a lower luminescence efficiency
particularly at the time of a high-current density. The material of
the present invention has a relatively short phosphorescence life
thus exhibiting a high phosphorescence quantum yield, and is
therefore suitable as a luminescence material for an EL device. The
present inventors further consider that the improved performance is
attributable to the following.
[0115] A difference between a photo-absorption spectrum peak
wavelength caused by transition from a single ground state to an
excited triplet state and a maximum peak wavelength of luminescence
spectrum is generally called a Stokes' shift. The difference in
peak wavelength is considered to be caused by a change in energy
state of triplet excitons affected by other ground state energy
levels. The change in energy state is associated with the Stokes'
shift, and a larger amount of the shift generally results in a
lowering in maximum luminescence intensity and a broadening of
luminescence spectrum leading to a deterioration in
monochromaticity of luminescence color. This effect appears
particularly remarkably in a red region having a short transition
width from the singlet to the triplet.
[0116] For example, as for the isoquinoline-type iridium complexes
of the present invention,
tris(1-phenylisoquinoline-C.sup.2,N)iridium (III) (Example Compound
No. 1 in Tables 1 to 23 appearing hereafter; abbreviated as
Ir(PiQ).sub.3), tris[1-(2-thienyl)-isoquinoline-C.sup.3,N]iridium
(III) (Example Compound No. 24, abbreviated as Ir(tiQ).sub.3), and
tris[1-(9,9-dimethylfluorene-2-yl)isoquinoline-C.sup.3,N]iridium
(III) (Example Compound 28, abbreviated as Ir(FliQ).sub.3)
exhibited Stokes' shifts of 37 nm, 55 nm and 33 nm, respectively,
and relative quantum yields of 0.66, 0.43 and 0.48,
respectively.
[0117] On the other hand, as for non-isoquinoline-type red
luminescence materials,
tris[1-thianaphthene-2-yl)pyridine-C.sup.3,N]iridium (III)
(abbreviated as Ir(BrP).sub.3) and
tris(1-(thianaphthene-2-yl)-4-trifluoromethylpyridine (abbreviated
as Ir(Bt.sub.5CF.sub.3Py).sub.3) exhibited remarkably longer
Stokes' shifts of 132 nm and 85 nm, respectively, and lower
relative quantum yields of 0.29 and 0.12, respectively, compared
with the compounds of the present invention.
[0118] Even such non-isoquinoline-type red luminescence materials
show high quantum yields not achieved by conventional materials,
red luminescence materials showing a smaller Stokes' shift, like
isoquinoline-type iridium complexes of the present invention, are
found to have a tendency of having a still higher quantum yield. A
smaller Stokes' shift is considered to provide a larger velocity
constant of energy radiation, a shorter phosphorescence life and
therefore a higher luminescence efficiency. Based on the above
consideration, the introduction of isoquinoline is considered to
result in a small Stokes' shift, an enhanced luminescence quantum
yield and a better chromaticity.
<<Nomenclature and Structural Expression of
Compounds>>
[0119] Now, some explanation is added to the manner of structural
identification of a metal coordination compound of the present
invention and the manner of allotting atomic position number as a
basis therefor with reference to Ir(PiQ).sub.3 (Example Compound
No. 1), for example. The metal coordination compound has a ligand
of 1-phenylisoquinoline of which position numbers are allotted as
follows:
##STR00005##
[0120] Accordingly, Ir(PiQ).sub.3 formed by coordination of three
1-phenylisoquinoline molecules, onto iridium with the position-2
carbon atom of the phenyl group and the nitrogen atom of the
isoquinoline ring is named as
tris(1-phenylisoquinoline-C.sup.2,N)iridium (III).
[0121] Ir(PiQ).sub.3 exhibits a high quantum yield as mentioned
above, but it has been also found that Ir(PiQ).sub.3 provided with
an additional substituent shows a further higher quantum yield in a
solution or a solid state film. For example, a class of
tris[1-alkylphenyl)isoquinoline-C.sup.2,N]iridium (III) formed by
attaching alkyl substituents at position-4 of the basic ligand
skeleton of 1-phenylisoquinoline exhibits still higher relative
quantum yields (i.e., quantum yields when Ir(ppy).sub.3 in a dilute
solution in toluene is taken to have a quantum yield of 1). More
specifically, the class of compounds have been found to exhibit
quantum yields as shown below depending on species of the alkyl
substituents. Remarkable increases in quantum yield have been
recognized at number of carbon atoms of 4 or more in the subsequent
group.
[0122] (1) --CH.sub.3=0.64
[0123] (2) --C(CH.sub.3).sub.3=0.7
[0124] (3) --C.sub.4H.sub.9=0.82
[0125] (4) --C.sub.6H.sub.13=0.88
[0126] (5) --C.sub.8H.sub.17=0.72
From the above results, the addition of a substituent to the above
skeleton to weaken the inter-molecular interaction is found to be
effective for increasing the luminescence quantum yield.
[0127] On the other hand, in the case of using resistance heating
vacuum deposition using a tungsten boat for device formation, a
material having a molecular weight of at most 1000 has been found
suitable in view of the device production process characteristic,
such as possibility of vacuum deposition at a low current and a
high rate.
[0128] More specifically, the above-mentioned class of alkyl
chain-added iridium complexes have a tendency of exhibiting a
higher vacuum deposition temperature at the time of device
formation. The entire molecular weights of thus-alkyl-substituted
Ir(PiQ).sub.3 derivatives are as follows depending on the species
of alkyl substituents as follows.
[0129] (1) --CH.sub.3=847
[0130] (2) --C(CH.sub.3).sub.3=973
[0131] (3) --C.sub.4H.sub.9=973
[0132] (4) --C.sub.6H.sub.13=1058
[0133] (5) --C.sub.8H.sub.17=1141
[0134] At the time of resistance heating vacuum deposition at
10.sup.-4 Pa, these materials required necessary currents for
vacuum deposition as follows depending on the species of alkyl
substituents.
[0135] (1) --CH.sub.3=58 amperes
[0136] (2) --C(CH.sub.3).sub.3=61 amperes
[0137] (3) --C.sub.4H.sub.9=61 amperes
[0138] (4) --C.sub.6H.sub.13=64 amperes
[0139] (5) --C.sub.8H.sub.17=67 amperes
[0140] Further, a metal coordination compound having a substituent
of fluorine atom or a polyfluorinated alkyl can weaken the
intermolecular interaction owing to fluorine atoms to lower the
vacuum deposition temperature, and is advantageous in that a metal
coordination compound of a larger molecular weight can be used as a
luminescence material without impairing the vacuum deposition
characteristic. For example, the substitution of a trifluoromethyl
group for one methyl group can lower the vacuum deposition
temperature by ca. 1.degree. C. while the molecular weight is
rather increased thereby.
[0141] By introducing an isoquinoline skeleton in a metal
coordination compound having a structure of a type represented by
the above formula (1) or (9), the luminescence wavelength can be
adjusted, and it has been found that the metal coordination
compound of the present invention wherein the isoquinoline skeleton
is bonded to the cyclic group A at its position-1, is unexpectedly
advantageous for increasing the luminescence wavelength (i.e.,
providing red luminescence).
[0142] On the other hand, while a known compound of
tetrakis(2-phenylpyridine-C.sup.2,N)(.mu.-dichloro)diiridium (III)
does not provide a substantial luminescence spectrum, a metal
coordination compound of the formula (7) having introduced an
isoquinoline skeleton has exhibited a strong luminescence spectrum.
From this fact, it is understood that a metal coordination compound
of the formula (7) is also suited as a luminescence material for an
EL device.
[0143] Further, by introducing an electron-attractive substituent
or an electron-donative substituent to the metal coordination
compound of the present invention, it is possible to adjust the
luminescence wavelength. Further, by introducing a substituent
group, such as an alkoxy group or a polyfluoroalkyl group, having a
large electronic effect and also a stereo-scopically large bulk
volume, it becomes possible to effect both a control of
luminescence wavelength and a suppression of density extinction due
to inter-molecular interaction. Further, the introduction of a
substituent group having little electronic effect but having a
stereoscopically large bulk volume, such as an alkyl group, is
considered to be able to suppress the density extraction without
changing the luminescence wavelength.
[0144] Further, by replacing one or two CH groups in the
isoquinoline ring of a metal coordination compound represented by
the formula (1) or (9), the luminescence wavelength can be adjusted
without introducing a substituent group.
[0145] Also from the above viewpoints, the metal coordination
compound of the present invention is suited as a luminescence
material for an organic EL device.
[0146] Further, a thermal stability is an important property for an
organic material constituting an organic EL device. The thermal
stability seriously affects the production stability at the time of
device production and device stability during operation under
current supply. For preparation of organic EL devices, a process of
vacuum deposition, spin coating or ink jetting is contemplated.
Particularly, in the vacuum deposition process, an organic material
is subjected to high temperature for certain period for vaporizing
the organic material by sublimation or evaporation and is deposited
onto the substrate. Accordingly, the thermal stability of a
component material is very important.
[0147] Further, also at the time of supplying electricity to the
device for causing luminescence, a Joule's heat is locally
generated due to passage of a high current. If a component material
has a low thermal stability, the material can cause a device
deterioration due to such heat. For example, the above-mentioned
Ir(PiQ).sub.3 and
bis(1-phenylisoquinoline-C.sup.2,N)(acetylacetonato)iridium (III)
(Example Compound No. 42, abbreviated as Ir(PiQ).sub.2acac)
exhibited decomposition temperatures of 380.degree. C. and
340.degree. C., respectively, under nitrogen flow, thus providing a
substantial difference in decomposition temperature. More
specifically, under a certain vacuum deposition condition,
Ir(PiQ).sub.3acac caused an appreciable decomposition in a vacuum
deposition chamber, but Ir(PiQ).sub.3 did not cause appreciable
decomposition under the same condition. As a result of measurement
of decomposition degree under various conditions of vacuum
deposition, Ir(PiQ).sub.3 acac exhibited lower upper limits in
vacuum deposition speed or degree of vacuum in vacuum deposition,
thus exhibiting a narrower production margin at the time of mass
production. In this way, a material thermal stability seriously
affects the productivity.
[0148] In a comparative test, EL devices were prepared from the
above-mentioned two luminescence materials through vacuum
deposition under decomposition-free condition and subjected to
evaluation of luminance deterioration. As a result, when
electricity supply was started to provide an initial luminance of
5000 cd/m.sup.2, Ir(PiQ).sub.3 and Ir(PiQ).sub.2 acac exhibited
luminance half-attenuation periods in a ratio of ca. 3:1, so that
Ir(PiQ).sub.3 was substantially stable against electricity supply
as represented by a longer luminance half-attenuation period. In
this way, the thermal stability of a component material is a factor
determining the production stability and performance stability of a
device, so that a material having a high thermal stability is
desired.
[0149] It is believed that the ligand of the present invention, as
a result of introduction of isoquinoline skeleton, has a rigid
molecular structure, so as to suppress the formation of an
excitation-associated molecule resulting in thermal deactivation,
thus suppressing energy deactivation due to molecular movement.
Further, it is also believed that extinction processes are reduced
to result in an improved device performance. In an actual current
conduction test, the luminescence material of the present
invention, i.e., a metal coordination compound having a ligand
comprising en isoquinoline skeleton bonded to a cyclic group A at
its 1-position, showed a high stability.
[0150] More specifically, a tris(1-substituted isoquinolyl)-metal
coordination compound of n 0 in the formula (3) is generally
preferred in view of excellent thermal stability.
[0151] Accordingly, a luminescence material having a luminescence
wavelength of long-wavelength region (red luminescence) and a high
chemical stability as well as a high luminescence efficiency has
not been realized heretofore but can be realized by the
luminescence material of the present invention.
[0152] A high-efficiency luminescence device having a layer
structure as shown in FIGS. 1(a), (b) and (c) of the present
invention is applicable to a product requiring energy economization
or a high luminance. More specifically, the luminescence device is
applicable to a display apparatus, an illumination apparatus, a
printer light source or a backlight for a luminescence layer
display apparatus. As for a display apparatus, it allows a flat
panel display which is light in weight and provides a highly
recognizable display at a low energy consumption. As a printer
light source, the luminescence device of the present invention can
be used instead of a laser light source of a laser beam printer.
For the illumination apparatus or backlight, the energy
economization effect according to the present invention can be
utilized.
[0153] For the application to a display, a drive system using a
thin-film transistor (abbreviated as TFT) drive circuit according
to an active matrix-scheme, may be used. Hereinbelow, an embodiment
of using a device of the present invention in combination with an
active matrix substrate is briefly described with reference to FIG.
4.
[0154] FIG. 4 illustrates an embodiment of panel structure
comprising an EL device and drive means. The panel is provided with
a scanning signal driver, a data signal driver and a current supply
source which are connected to gate selection lines, data signal
lines and current supply lines, respectively. At each intersection
of the gate selection lines and the data signal lines, a display
pixel electrode is disposed. The scanning signal drive sequentially
selects the gate selection lines G1, G2, G3 . . . Gn, and in
synchronism herewith, picture signals are supplied from the data
signal driver to display a printer.
[0155] TFT switching devices are not particularly restricted, and
devices of a single crystal-silicon substrate, MIM devices or
devices of a-Si type can be easily applied.
[0156] On the ITO electrodes, one or more organic EL layers and a
cathode layer are sequentially disposed to provide an organic EL
display panel. By driving a display panel including a luminescence
layer comprising a luminescence material of the present invention,
it becomes possible to provide a display which exhibits a good
picture quality and is stable even for a long period display.
<<Brief Description of Synthesis Path>>
[0157] Some synthetic paths for providing a metal coordination
compound represented by the above-mentioned formula (1) are
illustrated below with reference to an iridium coordination
compound for example;
##STR00006##
[0158] Some specific structural examples of metal coordination
compounds used in the present invention are shown in Tables 1 to
Tables 23 appearing hereinafter, which are however only
representative examples and are not exhaustive. Ph to Iq10 shown in
Tables 1 to 23 represent partial structures shown below,
corresponding to the above-mentioned formula (3) (or partial
structures therein represented by formulae (2), and (4)-(6)) or
formula (3). Further, R1-R10 represent substituents in the Ph to
Iq10, and E, G and J represent substituents in the formula (5).
##STR00007## ##STR00008## ##STR00009## ##STR00010##
##STR00011##
TABLE-US-00001 TABLE 1 A B No M m n A B R1 R2 R3 R4 R5 R6 R7 R8 R9
R10 1 Ir 3 0 Ph Iq2 H H H H H H H H H H 2 Ir 3 0 Ph Iq2 H
##STR00012## H H H H H H H H 3 Ir 3 0 Ph Iq2 H H ##STR00013## H H H
H H H H 4 Ir 3 0 Ph Iq2 H ##STR00014## H H H ##STR00015## H H H H 5
Ir 3 0 Ph Iq2 H CH3 H H H H CF3 H H H 6 Ir 3 0 Ph Iq2 H H CH3 H H
CF3 H H H H 7 Ir 3 0 Ph Iq2 H ##STR00016## H H H H H H H H 8 Ir 3 0
Ph Iq2 H H ##STR00017## H H H H H H H 9 Ir 3 0 Ph Iq2 H
##STR00018## H H H H H H H H 10 Ir 3 0 Ph Iq2 H H ##STR00019## H H
H H H H H
TABLE-US-00002 TABLE 2 A No M m n A B R1 R2 R3 R4 11 Ir 3 0 Ph Iq2
H CF3 H H 12 Ir 3 0 Ph Iq2 H H CF3 H 13 Ir 3 0 Ph Iq2 H
##STR00020## H H 14 Ir 3 0 Ph Iq2 H H ##STR00021## H 15 Ir 3 0 Ph
Iq2 H ##STR00022## H H 16 Ir 3 0 Ph Iq2 H ##STR00023## H H 17 Ir 3
0 Ph Iq2 H OCH3 H H 18 Ir 3 0 Ph Iq2 H ##STR00024## H H B No R5 R6
R7 R8 R9 R10 11 H H H H H H 12 H H H H H H 13 H H H H H H 14 H H H
H H H 15 H H H H H H 16 H H H H H H 17 H H H H H H 18 H
##STR00025## H H H H
TABLE-US-00003 TABLE 3 A No M m n A B A' B' E G J R1 R2 R3 R4 19 Ir
3 0 Ph Iq2 -- -- -- -- -- H CH3 H H 20 Ir 3 0 Ph Iq2 -- -- -- -- --
H H CH3 H 21 Ir 3 0 Ph Iq2 -- -- -- -- -- H CH3 CH3 H 22 Ir 3 0 Ph
Iq2 -- -- -- -- -- H F H H 23 Ir 3 0 Ph Iq2 -- -- -- -- -- H H F H
24 Ir 3 0 Tn1 Iq2 -- -- -- -- -- H H -- -- 25 Ir 3 0 Tn3 Iq2 -- --
-- -- -- H H -- -- 26 Ir 3 0 Tn4 Iq2 -- -- -- -- -- H H -- -- 27 Ir
3 0 Np2 Iq2 -- -- -- -- -- H H -- -- 28 Ir 3 0 Fl Iq2 -- -- -- --
-- H H -- -- 29 Ir 3 0 Ph Iq5 -- -- -- -- -- H H H H 30 Ir 3 0 Fl
Iq5 -- -- -- -- -- H H H H 31 Ir 2 1 Ph Iq2 Ph Pr -- -- -- H H H H
32 Ir 2 1 Ph Iq2 Ph Pr -- -- -- H CH3 H H 33 Ir 2 1 Ph Iq2 Ph Pr --
-- -- H H CH3 H 34 Ir 2 1 Ph Iq2 Ph Pr -- -- -- H CH3 CH3 H 35 Ir 2
1 Ph Iq2 Ph Pr -- -- -- H F H H 36 Ir 2 1 Ph Iq2 Ph Pr -- -- -- H H
F H 37 Ir 2 1 Tn1 Iq2 Ph Pr -- -- -- H H -- -- 38 Ir 2 1 Tn3 Iq2 Ph
Pr -- -- -- H H -- -- 39 Ir 2 1 Tn4 Iq2 Ph Pr -- -- -- H H -- -- 40
Ir 2 1 Np2 Iq2 Ph Pr -- -- -- H H -- -- 41 Ir 2 1 Fl Iq2 Ph Pr --
-- -- H H -- -- 42 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H H H H H 43 Ir 2 1
Ph Iq2 -- -- CH3 CH3 H H CH3 H H 44 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H H
H CH3 H 45 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H H CH3 CH3 H 46 Ir 2 1 Ph
Iq2 -- -- CH3 CH3 H H F H H 47 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H H H F
H 48 Ir 2 1 Tn1 Iq2 -- -- CH3 CH3 H H H -- -- 49 Ir 2 1 Tn3 Iq2 --
-- CH3 CH3 H H H -- -- 50 Ir 2 1 Tn4 Iq2 -- -- CH3 CH3 H H H -- --
51 Ir 2 1 Np2 Iq2 -- -- CH3 CH3 H H H -- -- 52 Ir 2 1 Fl Iq2 -- --
CH3 CH3 H H H -- -- 53 Ir 2 1 Ph Iq2 -- -- CF3 CF3 H H H H H 54 Ir
2 1 Ph Iq2 -- -- CF3 CF3 H H CH3 H H 55 Ir 2 1 Ph Iq2 -- -- CF3 CF3
H H H CH3 H 56 Ir 2 1 Ph Iq2 -- -- CF3 CF3 H H CH3 CH3 H 57 Ir 2 1
Ph Iq2 -- -- CF3 CF3 H H F H H 58 Ir 2 1 Ph Iq2 -- -- CF3 CF3 H H H
F H 59 Ir 2 1 Tn1 Iq2 -- -- CF3 CF3 H H H -- -- 60 Ir 2 1 Tn3 Iq2
-- -- CF3 CF3 H H H -- -- A' B B' No R1 R2 R3 R4 R5 R6 R7 R8 R9 R10
R5 R6 R7 R8 19 -- -- -- -- H H H H H H -- -- -- -- 20 -- -- -- -- H
H H H H H -- -- -- -- 21 -- -- -- -- H H H H H H -- -- -- -- 22 --
-- -- -- H H H H H H -- -- -- -- 23 -- -- -- -- H H H H H H -- --
-- -- 24 -- -- -- -- H H H H H H -- -- -- -- 25 -- -- -- -- H H H H
H H -- -- -- -- 26 -- -- -- -- H H H H H H -- -- -- -- 27 -- -- --
-- H H H H H H -- -- -- -- 28 -- -- -- -- H H H H H H -- -- -- --
29 -- -- -- -- -- H H H H H -- -- -- -- 30 -- -- -- -- -- H H H H H
-- -- -- -- 31 H H H H H H H H H H H H H H 32 H H H H H H H H H H H
H H H 33 H H H H H H H H H H H H H H 34 H H H H H H H H H H H H H H
35 H H H H H H H H H H H H H H 36 H H H H H H H H H H H H H H 37 H
H H H H H H H H H H H H H 38 H H H H H H H H H H H H H H 39 H H H H
H H H H H H H H H H 40 H H H H H H H H H H H H H H 41 H H H H H H H
H H H H H H H 42 -- -- -- -- H H H H H H -- -- -- -- 43 -- -- -- --
H H H H H H -- -- -- -- 44 -- -- -- -- H H H H H H -- -- -- -- 45
-- -- -- -- H H H H H H -- -- -- -- 46 -- -- -- -- H H H H H H --
-- -- -- 47 -- -- -- -- H H H H H H -- -- -- -- 48 -- -- -- -- H H
H H H H -- -- -- -- 49 -- -- -- -- H H H H H H -- -- -- -- 50 -- --
-- -- H H H H H H -- -- -- -- 51 -- -- -- -- H H H H H H -- -- --
-- 52 -- -- -- -- H H H H H H -- -- -- -- 53 -- -- -- -- H H H H H
H -- -- -- -- 54 -- -- -- -- H H H H H H -- -- -- -- 55 -- -- -- --
H H H H H H -- -- -- -- 56 -- -- -- -- H H H H H H -- -- -- -- 57
-- -- -- -- H H H H H H -- -- -- -- 58 -- -- -- -- H H H H H H --
-- -- -- 59 -- -- -- -- H H H H H H -- -- -- -- 60 -- -- -- -- H H
H H H H -- -- -- --
TABLE-US-00004 TABLE 4 A No M m n A B A' B' E G J R1 R2 R3 R4 61 Ir
2 1 Tn4 Iq2 -- -- CF3 CF3 H H H -- -- 62 Ir 2 1 Np2 Iq2 -- -- CF3
CF3 H H H -- -- 63 Ir 2 1 Fl Iq2 -- -- CF3 CF3 H H H -- -- 64 Ir 1
2 Ph Iq2 Ph Pr -- -- -- H H H H 65 Ir 1 2 Ph Iq2 Ph Pr -- -- -- H
CH3 H H 66 Ir 1 2 Ph Iq2 Ph Pr -- -- -- H H CH3 H 67 Ir 1 2 Ph Iq2
Ph Pr -- -- -- H CH3 CH3 H 68 Ir 1 2 Ph Iq2 Ph Pr -- -- -- H F H H
69 Ir 1 2 Ph Iq2 Ph Pr -- -- -- H H F H 70 Ir 1 2 Tn1 Iq2 Ph Pr --
-- -- H H -- -- 71 Ir 1 2 Tn3 Iq2 Ph Pr -- -- -- H H -- -- 72 Ir 1
2 Tn4 Iq2 Ph Pr -- -- -- H H -- -- 73 Ir 1 2 Np2 Iq2 Ph Pr -- -- --
H H -- -- 74 Ir 1 2 Fl Iq2 Ph Pr -- -- -- H H -- -- 75 Ir 1 2 Ph
Iq2 -- -- CH3 CH3 H H H H H 76 Ir 1 2 Ph Iq2 -- -- CH3 CH3 H H CH3
H H 77 Ir 1 2 Ph Iq2 -- -- CH3 CH3 H H H CH3 H 78 Ir 1 2 Ph Iq2 --
-- CH3 CH3 H H CH3 CH3 H 79 Ir 1 2 Ph Iq2 -- -- CH3 CH3 H H F H H
80 Ir 1 2 Ph Iq2 -- -- CH3 CH3 H H H F H 81 Ir 3 0 Ph Iq2 -- -- --
-- -- H H H H 82 Ir 3 0 Ph Iq2 -- -- -- -- -- H H H H 83 Ir 3 0 Ph
Iq2 -- -- -- -- -- H H H H 84 Ir 3 0 Ph Iq2 -- -- -- -- -- H H F H
85 Ir 3 0 Ph Iq2 -- -- -- -- -- H H F H 86 Rh 3 0 Ph Iq2 -- -- --
-- -- H H H H 87 Rh 3 0 Tn1 Iq2 -- -- -- -- -- H H -- -- 88 Rh 3 0
Tn3 Iq2 -- -- -- -- -- H H -- -- 89 Rh 3 0 Np2 Iq2 -- -- -- -- -- H
H -- -- 90 Rh 3 0 Fl Iq2 -- -- -- -- -- H H -- -- 91 Rh 2 1 Ph Iq2
Ph Pr -- -- -- H H H H 92 Rh 2 1 Ph Iq2 Ph Pr -- -- -- H CH3 H H 93
Rh 2 1 Ph Iq2 Ph Pr -- -- -- H H CH3 H 94 Rh 2 1 Ph Iq2 -- -- CH3
CH3 H H H H H 95 Pt 2 0 Ph Iq2 -- -- -- -- -- H H H H 96 Pt 2 0 Ph
Iq2 -- -- -- -- -- H CH3 H H 97 Pt 2 0 Ph Iq2 -- -- -- -- -- H CH3
CH3 H 98 Pt 2 0 Ph Iq2 -- -- -- -- -- H F H H 99 Pt 2 0 Ph Iq2 --
-- -- -- -- H H F H 100 Pt 2 0 Tn1 Iq2 -- -- -- -- -- H H -- -- A'
B B' No R1 R2 R3 R4 R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 61 -- -- -- -- H
H H H H H -- -- -- -- 62 -- -- -- -- H H H H H H -- -- -- -- 63 --
-- -- -- H H H H H H -- -- -- -- 64 H H H H H H H H H H H H H H 65
H H H H H H H H H H H H H H 66 H H H H H H H H H H H H H H 67 H H H
H H H H H H H H H H H 68 H H H H H H H H H H H H H H 69 H H H H H H
H H H H H H H H 70 H H H H H H H H H H H H H H 71 H H H H H H H H H
H H H H H 72 H H H H H H H H H H H H H H 73 H H H H H H H H H H H H
H H 74 H H H H H H H H H H H H H H 75 -- -- -- -- H H H H H H -- --
-- -- 76 -- -- -- -- H H H H H H -- -- -- -- 77 -- -- -- -- H H H H
H H -- -- -- -- 78 -- -- -- -- H H H H H H -- -- -- -- 79 -- -- --
-- H H H H H H -- -- -- -- 80 -- -- -- -- H H H H H H -- -- -- --
81 -- -- -- -- H H H H F H -- -- -- -- 82 -- -- -- -- H H H H CF3 H
-- -- -- -- 83 -- -- -- -- H H H CF3 H H -- -- -- -- 84 -- -- -- --
H H H F H H -- -- -- -- 85 -- -- -- -- H H H CF3 H H -- -- -- -- 86
-- -- -- -- H H H H H H -- -- -- -- 87 -- -- -- -- H H H H H H --
-- -- -- 88 -- -- -- -- H H H H H H -- -- -- -- 89 -- -- -- -- H H
H H H H -- -- -- -- 90 -- -- -- -- H H H H H H -- -- -- -- 91 H H H
H H H H H H H H H H H 92 H H H H H H H H H H H H H H 93 H H H H H H
H H H H H H H H 94 -- -- -- -- H H H H H H -- -- -- -- 95 -- -- --
-- H H H H H H -- -- -- -- 96 -- -- -- -- H H H H H H -- -- -- --
97 -- -- -- -- H H H H H H -- -- -- -- 98 -- -- -- -- H H H H H H
-- -- -- -- 99 -- -- -- -- H H H H H H -- -- -- -- 100 -- -- -- --
H H H H H H -- -- -- --
TABLE-US-00005 TABLE 5 A No M m n A B A' B' E G J R1 R2 R3 R4 101
Pt 2 0 Tn3 Iq2 -- -- -- -- -- H H -- -- 102 Pt 1 1 Ph Iq2 Ph Pr --
-- -- H H H H 103 Pt 1 1 Ph Iq2 Ph Pr -- -- -- H H CH3 H 104 Pt 1 1
Ph Iq2 Ph Pr -- -- -- H CH3 CH3 H 105 Pt 1 1 Ph Iq2 Ph Pr -- -- --
H F H H 106 Pd 2 0 Ph Iq2 -- -- -- -- -- H H H H 107 Pd 2 0 Ph Iq2
-- -- -- -- -- H H CH3 H 108 Pd 2 0 Tn1 Iq2 -- -- -- -- -- H H --
-- 109 Pd 2 0 Tn3 Iq2 -- -- -- -- -- H H -- -- 110 Pd 1 1 Ph Iq2 Ph
Pr -- -- -- H H H H 111 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 H H H H 112
Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H H H H H 113 Ir 2 1 Ph Iq2 --
-- CH3 C4H9 CH3 H H H H 114 Ir 2 1 Tn1 Iq2 -- -- CH3 CH3 CH3 H H --
-- 115 Ir 2 1 Tn1 Iq2 -- -- C(CH3)3 C(CH3)3 H H H -- -- 116 Ir 2 1
Tn1 Iq2 -- -- CH3 C3H7 CH3 H H -- -- 117 Ir 2 1 Tn2 Iq2 -- -- CH3
CH3 CH3 H H -- -- 118 Ir 2 1 Tn2 Iq2 -- -- C(CH3)3 C(CH3)3 H H H --
-- 119 Ir 2 1 Tn2 Iq2 -- -- CH3 C6H13 CH3 H H -- -- 120 Ir 2 1 Tn3
Iq2 -- -- CH3 CH3 CH3 H H -- -- 121 Ir 2 1 Tn3 Iq2 -- -- C(CH3)3
C(CH3)3 H H H -- -- 122 Ir 2 1 Tn3 Iq2 -- -- CH3 C4H9 CH3 H H -- --
123 Ir 2 1 Tn4 Iq2 -- -- CH3 CH3 CH3 H H -- -- 124 Ir 2 1 Tn4 Iq2
-- -- C(CH3)3 C(CH3)3 H H H -- -- 125 Ir 2 1 Tn4 Iq2 -- -- CH3
C5H11 CH3 H H -- -- 126 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 H CH3 H H
127 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H H CH3 H H 128 Ir 2 1 Ph
Iq2 -- -- CH3 C4H9 CH3 H CH3 H H 129 Ir 2 1 Fl Iq2 -- -- CH3 CH3
CH3 H H -- -- 130 Ir 2 1 Fl Iq2 -- -- C(CH3)3 C(CH3)3 H H H -- --
131 Ir 2 1 Fl Iq2 -- -- CH3 C4H9 CH3 H H -- -- 132 Ir 2 1 Np1 Iq2
-- -- CH3 CH3 CH3 H H -- -- 133 Ir 2 1 Np1 Iq2 -- -- C(CH3)3
C(CH3)3 H H H -- -- 134 Ir 2 1 Np1 Iq2 -- -- CH3 C4H9 CH3 H H -- --
135 Ir 3 0 Ph Iq2 -- -- -- -- -- H C2H5 H H 136 Ir 2 1 Ph Iq2 Ph Pr
-- -- -- H C2H5 H H 137 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H H C2H5 H H
138 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 H C2H5 H H 139 Ir 2 1 Ph Iq2 --
-- C(CH3)3 C(CH3)3 H H C2H5 H H 140 Ir 2 1 Ph Iq2 -- -- CH3 C4H9
CH3 H C2H5 H H A' B B' No R1 R2 R3 R4 R5 R6 R7 R8 R9 R10 R5 R6 R7
R8 101 -- -- -- -- H H H H H H -- -- -- -- 102 H H H H H H H H H H
H H H H 103 H H H H H H H H H H H H H H 104 H H H H H H H H H H H H
H H 105 H H H H H H H H H H H H H H 106 -- -- -- -- H H H H H H --
-- -- -- 107 -- -- -- -- H H H H H H -- -- -- -- 108 -- -- -- -- H
H H H H H -- -- -- -- 109 -- -- -- -- H H H H H H -- -- -- -- 110 H
H H H H H H H H H H H H H 111 -- -- -- -- H H H H H H -- -- -- --
112 -- -- -- -- H H H H H H -- -- -- -- 113 -- -- -- -- H H H H H H
-- -- -- -- 114 -- -- -- -- H H H H H H -- -- -- -- 115 -- -- -- --
H H H H H H -- -- -- -- 116 -- -- -- -- H H H H H H -- -- -- -- 117
-- -- -- -- H H H H H H -- -- -- -- 118 -- -- -- -- H H H H H H --
-- -- -- 119 -- -- -- -- H H H H H H -- -- -- -- 120 -- -- -- -- H
H H H H H -- -- -- -- 121 -- -- -- -- H H H H H H -- -- -- -- 122
-- -- -- -- H H H H H H -- -- -- -- 123 -- -- -- -- H H H H H H --
-- -- -- 124 -- -- -- -- H H H H H H -- -- -- -- 125 -- -- -- -- H
H H H H H -- -- -- -- 126 -- -- -- -- H H H H H H -- -- -- -- 127
-- -- -- -- H H H H H H -- -- -- -- 128 -- -- -- -- H H H H H H --
-- -- -- 129 -- -- -- -- H H H H H H -- -- -- -- 130 -- -- -- -- H
H H H H H -- -- -- -- 131 -- -- -- -- H H H H H H -- -- -- -- 132
-- -- -- -- H H H H H H -- -- -- -- 133 -- -- -- -- H H H H H H --
-- -- -- 134 -- -- -- -- H H H H H H -- -- -- -- 135 -- -- -- -- H
H H H H H -- -- -- -- 136 H H H H H H H H H H H H H H 137 -- -- --
-- H H H H H H -- -- -- -- 138 -- -- -- -- H H H H H H -- -- -- --
139 -- -- -- -- H H H H H H -- -- -- -- 140 -- -- -- -- H H H H H H
-- -- -- --
TABLE-US-00006 TABLE 6-1 (continued to Table 6-2) No M m n A B A'
B' E G J B'' 141 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 142 Ir 2 1 Ph Iq2
-- -- -- -- -- Pr 143 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 144 Ir 3 0
Ph Iq2 -- -- -- -- -- -- 145 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 146 Ir
3 0 Ph Iq2 -- -- -- -- -- -- 147 Ir 2 1 Ph Iq2 Ph Pr -- -- -- --
148 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 149 Ir 2 1 Ph Iq2 -- -- CH3
CH3 CH3 -- 150 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 151 Ir 2 1
Ph Iq2 -- -- CH3 C4H9 CH3 -- 152 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
153 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 154 Ir 2 1 Ph Iq2 -- -- -- --
-- Iq2 155 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 156 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 157 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 158 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 159 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 160 Ir 3 0 Ph
Iq2 -- -- -- -- -- -- 161 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 162 Ir 2
1 Ph Iq2 Ph Pr -- -- -- -- 163 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 164
Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 165 Ir 2 1 Ph Iq2 -- -- C(CH3)3
C(CH3)3 H -- 166 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 167 Ir 2 1 Ph
Iq2 -- -- -- -- -- Pr 168 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 169 Ir 2
1 Ph Iq2 -- -- -- -- -- Iq2 170 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 171
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 172 Ir 3 0 Ph Iq2 -- -- -- -- -- --
173 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 174 Ir 2 1 Ph Iq2 -- -- CH3 CH3
H -- 175 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 176 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H -- 177 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 178 Ir
2 1 Ph Iq2 -- -- -- -- -- Pr 179 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
180 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2
TABLE-US-00007 TABLE 6-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 141 H C2H5 H H --
-- -- -- H H H H H H -- -- -- -- H H H H -- -- 142 H C2H5 H H -- --
-- -- H H H H H H -- -- -- -- H H C4H9 H -- -- 143 H C2H5 H H -- --
-- -- H H H H H H -- -- -- -- H H H H H H 144 H C3H7 H H -- -- --
-- H H H H H H -- -- -- -- -- -- -- -- -- -- 145 H C3H7 H H -- --
-- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 146 H CH(CH3)2 H H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 147 H C3H7 H
H H H H H H H H H H H H H H H -- -- -- -- -- -- 148 H C3H7 H H --
-- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 149 H C3H7 H H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 150 H C3H7 H
H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 151 H C3H7
H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 152 H
C3H7 H H -- -- -- -- H H H H H H -- -- -- -- H H H H -- -- 153 H
C3H7 H H -- -- -- -- H H H H H H -- -- -- -- H H C4H9 H -- -- 154 H
C3H7 H H -- -- -- -- H H H H H H -- -- -- -- H H H H H H 155 H H H
H -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 156 H H H H
-- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 157 H CH3
H H -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 158 H CH3
H H -- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 159 H
C4H9 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 160
H C4H9 H H -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- --
161 H C4H9 H H -- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- --
-- -- 162 H C4H9 H H H H H H H H H H H H H H H H -- -- -- -- -- --
163 H C4H9 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- --
-- 164 H C4H9 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- --
-- -- 165 H C4H9 H H -- -- -- -- H H H H H H -- -- -- -- -- -- --
-- -- -- 166 H C4H9 H H -- -- -- -- H H H H H H -- -- -- -- -- --
-- -- -- -- 167 H C4H9 H H -- -- -- -- H H H H H H -- -- -- -- H H
H H -- -- 168 H C4H9 H H -- -- -- -- H H H H H H -- -- -- -- H H
C4H9 H -- -- 169 H C4H9 H H -- -- -- -- H H H H H H -- -- -- -- H H
H H H H 170 H C(CH3)3 H H -- -- -- -- H H H H H H -- -- -- -- -- --
-- -- -- -- 171 H C(CH3)3 H H -- -- -- -- H H H F H H -- -- -- --
-- -- -- -- -- -- 172 H C(CH3)3 H H -- -- -- -- H H H H C6H13 H --
-- -- -- -- -- -- -- -- -- 173 H C(CH3)3 H H H H H H H H H H H H H
H H H -- -- -- -- -- -- 174 H C(CH3)3 H H -- -- -- -- H H H H H H
-- -- -- -- -- -- -- -- -- -- 175 H C(CH3)3 H H -- -- -- -- H H H H
H H -- -- -- -- -- -- -- -- -- -- 176 H C(CH3)3 H H -- -- -- -- H H
H H H H -- -- -- -- -- -- -- -- -- -- 177 H C(CH3)3 H H -- -- -- --
H H H H H H -- -- -- -- -- -- -- -- -- -- 178 H C(CH3)3 H H -- --
-- -- H H H H H H -- -- -- -- H H H H -- -- 179 H C(CH3)3 H H -- --
-- -- H H H H H H -- -- -- -- H H C4H9 H -- -- 180 H C(CH3)3 H H --
-- -- -- H H H H H H -- -- -- -- H H H H H H
TABLE-US-00008 TABLE 7-1 (continued to Table 7-2) No M m n A B A'
B' E G J B'' 181 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 182 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 183 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 184 Ir 2 1 Ph
Iq2 Ph Pr -- -- -- -- 185 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 186 Ir 2
1 Ph Iq2 -- -- CH3 CH3 CH3 -- 187 Ir 2 1 Ph Iq2 -- -- C(CH3)3
C(CH3)3 H -- 188 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 189 Ir 2 1 Ph
Iq2 -- -- -- -- -- Pr 190 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 191 Ir 2
1 Ph Iq2 -- -- -- -- -- Iq2 192 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 193
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 194 Ir 3 0 Ph Iq2 -- -- -- -- -- --
195 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 196 Ir 2 1 Ph Iq2 -- -- CH3 CH3
H -- 197 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 198 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H -- 199 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 200 Ir
2 1 Ph Iq2 -- -- -- -- -- Pr 201 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
202 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 203 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 204 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 205 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 206 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 207 Ir 2 1 Ph Iq2
-- -- CH3 CH3 H -- 208 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 209 Ir 2
1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 210 Ir 2 1 Ph Iq2 -- -- CH3
C4H9 CH3 -- 211 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 212 Ir 2 1 Ph Iq2
-- -- -- -- -- Pr 213 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 214 Ir 3 0
Ph Iq2 -- -- -- -- -- -- 215 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 216 Ir
3 0 Ph Iq2 -- -- -- -- -- -- 217 Ir 2 1 Ph Iq2 Ph Pr -- -- -- --
218 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 219 Ir 2 1 Ph Iq2 -- -- CH3
CH3 CH3 -- 220 Ir 3 0 Ph Iq2 -- -- -- -- -- --
TABLE-US-00009 TABLE 7-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 181 H C5H11 H H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 182 H C5H11 H
H -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 183 H C5H11
H H -- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 184 H
C5H11 H H H H H H H H H H H H H H H H -- -- -- -- -- -- 185 H C5H11
H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 186 H
C5H11 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 187
H C5H11 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- --
188 H C5H11 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- --
-- 189 H C5H11 H H -- -- -- -- H H H H H H -- -- -- -- H H H H --
-- 190 H C5H11 H H -- -- -- -- H H H H H H -- -- -- -- H H C4H9 H
-- -- 191 H C5H11 H H -- -- -- -- H H H H H H -- -- -- -- H H H H H
H 192 H C6H13 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- --
-- -- 193 H C6H13 H H -- -- -- -- H H H F H H -- -- -- -- -- -- --
-- -- -- 194 H C6H13 H H -- -- -- -- H H H H C6H13 H -- -- -- -- --
-- -- -- -- -- 195 H C6H13 H H H H H H H H H H H H H H H H -- -- --
-- -- -- 196 H C6H13 H H -- -- -- -- H H H H H H -- -- -- -- -- --
-- -- -- -- 197 H C6H13 H H -- -- -- -- H H H H H H -- -- -- -- --
-- -- -- -- -- 198 H C6H13 H H -- -- -- -- H H H H H H -- -- -- --
-- -- -- -- -- -- 199 H C6H13 H H -- -- -- -- H H H H H H -- -- --
-- -- -- -- -- -- -- 200 H C6H13 H H -- -- -- -- H H H H H H -- --
-- -- H H H H -- -- 201 H C6H13 H H -- -- -- -- H H H H H H -- --
-- -- H H C4H9 H -- -- 202 H C6H13 H H -- -- -- -- H H H H H H --
-- -- -- H H H H H H 203 H C7H15 H H -- -- -- -- H H H H H H -- --
-- -- -- -- -- -- -- -- 204 H C7H15 H H -- -- -- -- H H H F H H --
-- -- -- -- -- -- -- -- -- 205 H C7H15 H H -- -- -- -- H H H H
C6H13 H -- -- -- -- -- -- -- -- -- -- 206 H C7H15 H H H H H H H H H
H H H H H H H -- -- -- -- -- -- 207 H C7H15 H H -- -- -- -- H H H H
H H -- -- -- -- -- -- -- -- -- -- 208 H C7H15 H H -- -- -- -- H H H
H H H -- -- -- -- -- -- -- -- -- -- 209 H C7H15 H H -- -- -- -- H H
H H H H -- -- -- -- -- -- -- -- -- -- 210 H C7H15 H H -- -- -- -- H
H H H H H -- -- -- -- -- -- -- -- -- -- 211 H C7H15 H H -- -- -- --
H H H H H H -- -- -- -- H H H H -- -- 212 H C7H15 H H -- -- -- -- H
H H H H H -- -- -- -- H H C4H9 H -- -- 213 H C7H15 H H -- -- -- --
H H H H H H -- -- -- -- H H H H H H 214 H C8H17 H H -- -- -- -- H H
H H H H -- -- -- -- -- -- -- -- -- -- 215 H C8H17 H H -- -- -- -- H
H H F H H -- -- -- -- -- -- -- -- -- -- 216 H C8H17 H H -- -- -- --
H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 217 H C8H17 H H H H H
H H H H H H H H H H H -- -- -- -- -- -- 218 H C8H17 H H -- -- -- --
H H H H H H -- -- -- -- -- -- -- -- -- -- 219 H C8H17 H H -- -- --
-- H H H H H H -- -- -- -- -- -- -- -- -- -- 220 H H H H -- -- --
-- H H H C8H17 H H -- -- -- -- -- -- -- -- -- --
TABLE-US-00010 TABLE 8-1 (continued to Table 8-2) No M m n A B A'
B' E G J B'' 221 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 222 Ir 2 1 Ph
Iq2 -- -- CH3 CH3 H -- 223 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 224 Ir 2
1 Ph Iq2 -- -- -- -- -- Iq2 225 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 226
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 227 Ir 3 0 Ph Iq2 -- -- -- -- -- --
228 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 229 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 230 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 231 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 232 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 233 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 234 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 235 Ir 2 1 Ph
Iq2 -- -- -- -- -- Iq2 236 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 237 Ir 3
0 Ph Iq2 -- -- -- -- -- -- 238 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 239
Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 240 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H
-- 241 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 242 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H -- 243 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 244 Ir
2 1 Ph Iq2 -- -- -- -- -- Pr 245 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
246 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 247 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 248 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 249 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 250 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 251 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 252 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 253 Ir 3 0 Ph
Iq2 -- -- -- -- -- -- 254 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 255 Ir 3
0 Ph Iq2 -- -- -- -- -- -- 256 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 257
Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 258 Ir 3 0 Ph Iq2 -- -- -- -- --
-- 259 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 260 Ir 3 0 Ph Iq2 -- -- --
-- -- --
TABLE-US-00011 TABLE 8-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 221 H C8H17 H H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 222 H F CH3 H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 223 H C8H17 H
H -- -- -- -- H H H H H H -- -- -- -- H H C4H9 H -- -- 224 H C8H17
H H -- -- -- -- H H H H H H -- -- -- -- H H H H H H 225 H C9H19 H H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 226 H F CH3 H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 227 H H F H
-- -- -- -- H H H H CF3 H -- -- -- -- -- -- -- -- -- -- 228 H F H H
-- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 229 H F H H
-- -- -- -- H H H CF3 H H -- -- -- -- -- -- -- -- -- -- 230 H F H H
-- -- -- -- H H H H F H -- -- -- -- -- -- -- -- -- -- 231 H F H H
-- -- -- -- H H H H CF3 H -- -- -- -- -- -- -- -- -- -- 232 F H F H
-- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 233 F H F H
-- -- -- -- H H H CF3 H H -- -- -- -- H H H H -- -- 234 H C9H19 H H
-- -- -- -- H H H H H H -- -- -- -- H H C4H9 H -- -- 235 H C9H19 H
H -- -- -- -- H H H H H H -- -- -- -- H H H H H H 236 H C10H21 H H
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 237 H C10H21
H H -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 238 H
C10H21 H H -- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- --
-- 239 H C10H21 H H H H H H H H H H H H H H H H -- -- -- -- -- --
240 H H H H -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- --
241 H C10H21 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- --
-- 242 H C10H21 H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- --
-- -- 243 H C10H21 H H -- -- -- -- H H H H H H -- -- -- -- -- -- --
-- -- -- 244 H C10H21 H H -- -- -- -- H H H H H H -- -- -- -- H H H
H -- -- 245 H C10H21 H H -- -- -- -- H H H H H H -- -- -- -- H H
C4H9 H -- -- 246 H C10H21 H H -- -- -- -- H H H H H H -- -- -- -- H
H H H H H 247 H C11H23 H H -- -- -- -- H H H H H H -- -- -- -- --
-- -- -- -- -- 248 F H F H -- -- -- -- H H H H F H -- -- -- -- --
-- -- -- -- -- 249 H H H H -- -- -- -- H H H H CF3 H -- -- -- -- --
-- -- -- -- -- 250 F F F H -- -- -- -- H H H CF3 H H -- -- -- -- --
-- -- -- -- -- 251 F F F H -- -- -- -- H H H F H H -- -- -- -- --
-- -- -- -- -- 252 F F F H -- -- -- -- H H H H F H -- -- -- -- --
-- -- -- -- -- 253 F F F H -- -- -- -- H H H H CF3 H -- -- -- -- --
-- -- -- -- -- 254 H CF3 H H -- -- -- -- H H H F H H -- -- -- -- --
-- -- -- -- -- 255 H CF3 H H -- -- -- -- H H H CF3 H H -- -- -- --
-- -- -- -- -- -- 256 H CF3 H H -- -- -- -- H H H H F H -- -- -- --
-- -- -- -- -- -- 257 H C11H23 H H -- -- -- -- H H H H H H -- -- --
-- H H H H H H 258 H C12H25 H H -- -- -- -- H H H H H H -- -- -- --
-- -- -- -- -- -- 259 H C12H25 H H -- -- -- -- H H H F H H -- -- --
-- -- -- -- -- -- -- 260 H CF3 H H -- -- -- -- H H H H CF3 H -- --
-- -- -- -- -- -- -- --
TABLE-US-00012 TABLE 9-1 (continued to Table 9-2) No M m n A B A'
B' E G J B'' 261 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 262 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 263 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 264 Ir 3 0 Ph
Iq2 -- -- -- -- -- -- 265 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 266 Ir 3
0 Ph Iq2 -- -- -- -- -- -- 267 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 268
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 269 Ir 3 0 Ph Iq2 -- -- -- -- -- --
270 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 271 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 272 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 273 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 274 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 275 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 276 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 277 Ir 3 0 Ph
Iq2 -- -- -- -- -- -- 278 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H --
279 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 280 Ir 2 1 Ph Iq2 -- -- -- --
-- Pr 281 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 282 Ir 2 1 Ph Iq2 Ph Iq2
-- -- -- -- 283 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 284 Ir 2 1 Ph Iq2
Ph Iq2 -- -- -- -- 285 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 286 Ir 2 1
Ph Iq2 Ph Iq2 -- -- -- -- 287 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 288
Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 289 Ir 2 1 Ph Iq2 Ph Iq2 -- -- --
-- 290 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 291 Ir 2 1 Ph Iq2 Ph Iq2 --
-- -- -- 292 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 293 Ir 2 1 Ph Iq2 Ph
Iq2 -- -- -- -- 294 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 295 Ir 2 1 Ph
Iq2 Ph Iq2 -- -- -- -- 296 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 297 Ir
2 1 Ph Iq2 Ph Iq2 -- -- -- -- 298 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- --
299 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 300 Ir 2 1 Ph Iq2 Ph Iq2 -- --
-- --
TABLE-US-00013 TABLE 9-2 A A' B No R1 R2 R3 R4 R1 R2 R3 R4 R5 R6 R7
R8 261 H C12H25 H H H H H H H H H H 262 H H CF3 H -- -- -- -- H H H
H 263 H H CF3 H -- -- -- -- H H H H 264 H H CF3 H -- -- -- -- H H H
H 265 H H CF3 H -- -- -- -- H H H F 266 H H CF3 H -- -- -- -- H H H
CF3 267 F F F F -- -- -- -- H H H H 268 F F F F -- -- -- -- H H H H
269 H C13H27 H H -- -- -- -- H H H H 270 H H C7H15O H -- -- -- -- H
H H H 271 H C15H31 H H -- -- -- -- H H H H 272 F F F F -- -- -- --
H H H CF3 273 H CF3O H H -- -- -- -- H H H H 274 H C3H7O H H -- --
-- -- H H H H 275 H C4H9O H H -- -- -- -- H H H H 276 H C18H37 H H
H H H H H H H H 277 H C19H39 H H -- -- -- -- H H H H 278 H C19H39 H
H -- -- -- -- H H H H 279 H C20H41 H H -- -- -- -- H H H H 280 H
C20H41 H H -- -- -- -- H H H H 281 H CH3 H H H H H H H H H H 282 H
C2H5 H H H H H H H H H H 283 H C3H7 H H H H H H H H H H 284 H C4H9
H H H H H H H H H H 285 H C(CH3)3 H H H H H H H H H H 286 H C5H11 H
H H H H H H H H H 287 H C6H13 H H H H H H H H H H 288 H C7H15 H H H
H H H H H H H 289 H C8H17 H H H H H H H H H H 290 H C9H19 H H H H H
H H H H H 291 H C10H21 H H H H H H H H H H 292 H C11H23 H H H H H H
H H H H 293 H C12H25 H H H H H H H H H F 294 H C15H31 H H H F H H H
H H H 295 H C18H37 H H H H CF3 H H H H H 296 H C20H41 H H H H H H H
H H --C.ident.CC4H9 297 H H H H H CH3 H H H H H H 298 H H H H H
C2H5 H H H H H H 299 H H H H H C3H7 H H H H H H 300 H H H H H C4H9
H H H H H H B B' B'' No R9 R10 R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 261 H
H H H H H -- -- -- -- -- -- 262 H H -- -- -- -- -- -- -- -- -- --
263 F H -- -- -- -- -- -- -- -- -- -- 264 CF3 H -- -- -- -- -- --
-- -- -- -- 265 H H -- -- -- -- -- -- -- -- -- -- 266 H H -- -- --
-- -- -- -- -- -- -- 267 H H -- -- -- -- -- -- -- -- -- -- 268 CF3
H -- -- -- -- -- -- -- -- -- -- 269 H H -- -- -- -- -- -- -- -- --
-- 270 H H -- -- -- -- -- -- -- -- -- -- 271 H H -- -- -- -- -- --
-- -- -- -- 272 H H -- -- -- -- -- -- -- -- -- -- 273 H H -- -- --
-- -- -- -- -- -- -- 274 H H -- -- -- -- -- -- -- -- -- -- 275 H H
-- -- -- -- -- -- -- -- -- -- 276 H H H H H H -- -- -- -- -- -- 277
H H -- -- -- -- -- -- -- -- -- -- 278 H H -- -- -- -- -- -- -- --
-- -- 279 H H -- -- -- -- -- -- -- -- -- -- 280 H H -- -- -- -- --
-- H H H H 281 H H H H H H H H -- -- -- -- 282 H H H H H H H H --
-- -- -- 283 H H H H H H H H -- -- -- -- 284 H H H H H H H H -- --
-- -- 285 H H H H H H H H -- -- -- -- 286 H H H H H H H H -- -- --
-- 287 H H H H H H H H -- -- -- -- 288 H H H H H H H H -- -- -- --
289 H H H H H H H H -- -- -- -- 290 H H H H H H H H -- -- -- -- 291
H H H H H H H H -- -- -- -- 292 H H H H H H H H -- -- -- -- 293 H H
H H H H H H -- -- -- -- 294 H H H H H H H H -- -- -- -- 295 H H H H
H H H H -- -- -- -- 296 H H H H H H H H -- -- -- -- 297 H H -- --
-- -- -- -- -- -- -- -- 298 H H -- -- -- -- -- -- -- -- -- -- 299 H
H -- -- -- -- -- -- -- -- -- -- 300 H H -- -- -- -- -- -- -- -- --
--
TABLE-US-00014 TABLE 10-1 (continued to Table 10-2) No M m n A B A'
B' 301 Ir 2 1 Ph Iq2 Ph Iq2 302 Ir 2 1 Ph Iq2 Ph Iq2 303 Ir 2 1 Ph
Iq2 Ph Iq2 304 Ir 2 1 Ph Iq2 Ph Iq2 305 Ir 2 1 Ph Iq2 Ph Iq2 306 Ir
2 1 Ph Iq2 Ph Iq2 307 Ir 2 1 Ph Iq2 Ph Iq2 308 Ir 2 1 Ph Iq2 Ph Iq2
309 Ir 2 1 Ph Iq2 Ph Iq2 310 Ir 2 1 Ph Iq2 Ph Iq2 311 Ir 2 1 Ph Iq2
Ph Iq2 312 Ir 2 1 Ph Iq2 Ph Iq2 313 Ir 3 0 Ph Iq2 -- -- 314 Ir 3 0
Ph Iq2 -- -- 315 Ir 3 0 Ph Iq2 -- -- 316 Ir 3 0 Ph Iq2 -- -- 317 Ir
3 0 Ph Iq2 -- -- 318 Ir 3 0 Ph Iq2 -- -- 319 Ir 3 0 Ph Iq2 -- --
320 Ir 3 0 Ph Iq2 -- -- 321 Ir 3 0 Ph Iq2 -- -- 322 Ir 3 0 Ph Iq2
-- -- 323 Ir 3 0 Ph Iq2 -- -- 324 Ir 3 0 Ph Iq2 -- -- 325 Ir 3 0 Ph
Iq2 -- -- 326 Ir 3 0 Ph Iq2 -- -- 327 Ir 3 0 Ph Iq2 -- -- 328 Ir 3
0 Ph Iq2 -- -- 329 Ir 2 1 Ph Iq2 Ph Iq2 330 Ir 2 1 Ph Iq2 Ph Iq2
331 Ir 2 1 Ph Iq2 Ph Iq2 332 Ir 2 1 Ph Iq2 Ph Iq2 333 Ir 2 1 Ph Iq2
Ph Iq2 334 Ir 2 1 Ph Iq2 Ph Iq2 335 Ir 3 0 Ph Iq2 Ph Iq2 336 Ir 2 1
Ph Iq2 Ph Iq2 337 Ir 2 1 Ph Iq2 Ph Iq2 338 Ir 2 1 Ph Iq2 Ph Iq2 339
Ir 2 1 Ph Iq2 Ph Iq2 340 Ir 2 1 Ph Iq2 Ph Iq2
TABLE-US-00015 TABLE 10-2 A A' B No R1 R2 R3 R4 R1 R2 R3 R4 R5 R6
301 H H H H H C(CH3)3 H H H H 302 H H H H H C5H11 H H H H 303 H H H
H H C6H13 H H H H 304 H H H H H C7H15 H H H H 305 H H H H H C8H17 H
H H H 306 H CH2OC5H11 H H H C9H19 H H H H 307 H H H H H C10H21 H H
H H 308 H H H H H C11H23 H H H H 309 H H H H H C12H25 H H H H 310 H
H H H H C15H31 H H H H 311 H H H H H C18H37 H H H H 312 H H H H H
C20H41 H H H H 313 H H CH3 H -- -- -- -- H H 314 H H C2H5 H -- --
-- -- H H 315 H H CH(CH3)2 H -- -- -- -- H H 316 H H C4H9 H -- --
-- -- H H 317 H H C(CH3)3 H -- -- -- -- H H 318 H H C5H11 H -- --
-- -- H H 319 H H C6H13 H -- -- -- -- H H 320 H H C7H15 H -- -- --
-- H H 321 H H C8H17 H -- -- -- -- H H 322 H H C9H19 H -- -- -- --
H H 323 H H C10H21 H -- -- -- -- H H 324 H H C11H23 H -- -- -- -- H
H 325 H H C12H25 H -- -- -- -- H H 326 H H C15H31 H -- -- -- -- H H
327 H H C18H37 H -- -- -- -- H H 328 H H C20H41 H -- -- -- -- H H
329 H H CH3 H H H H H H H 330 H H C2H5 H H H H H H H 331 H H C3H7 H
H H H H H H 332 H H C4H9 H H H H H H H 333 H H C(CH3)3 H H H H H H
H 334 H H C5H11 H H H H H H H 335 H H C6H13 H H H H H H H 336 H H
C7H15 H H H H H H H 337 H H C8H17 H H H H H H H 338 H H C9H19 H H H
H H H H 339 H H C10H21 H H H H H H H 340 H H C11H23 H H H H H H H B
B' No R7 R8 R9 R10 R5 R6 R7 R8 R9 R10 301 H H H H H H H H H H 302 H
H H H H H H H H H 303 H H H H H H H H H H 304 H H H H H H H H H H
305 H H H H H H H H H H 306 H H H H H H H H H H 307 H H H H H H H H
H H 308 H H H H H H H H H H 309 H H H H H H H H H H 310 H
--CH.dbd.CH--CH3 H H H H H H H H 311 H H H H H H H H H H 312 H H H
H H H H H H H 313 H H H H -- -- -- -- -- -- 314 H H H H -- -- -- --
-- -- 315 H H H H -- -- -- -- -- -- 316 H H H H -- -- -- -- -- --
317 H H H H -- -- -- -- -- -- 318 H H H H -- -- -- -- -- -- 319 H H
H H -- -- -- -- -- -- 320 H H H H -- -- -- -- -- -- 321 H H H H --
-- -- -- -- -- 322 H H H H -- -- -- -- -- -- 323 H H H H -- -- --
-- -- -- 324 H H H H -- -- -- -- -- -- 325 H H H H -- -- -- -- --
-- 326 H COOC6H13 H H -- -- -- -- -- -- 327 H H H H -- -- -- -- --
-- 328 H OCH2C3F7 H H -- -- -- -- -- -- 329 H H H H H H H H H H 330
H H H H H H H H H H 331 H H H H H H H H H H 332 H H H H H H H H H H
333 H H H H H H H H H H 334 H H H H H H H H H H 335 H H H H H H H H
H H 336 H H H H H H H H H H 337 H H H H H H H H H H 338 H H H H H H
H H H H 339 H H H H H H H H H H 340 H H H H H H H H H H
TABLE-US-00016 TABLE 11-1 (continued to Table 11-2) No M m n A B A'
B' E G J B'' 341 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 342 Ir 2 1 Ph Iq2
Ph Iq2 -- -- -- -- 343 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 344 Ir 2 1
Ph Iq2 Ph Iq2 -- -- -- -- 345 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 346
Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 347 Ir 2 1 Ph Iq2 Ph Iq2 -- -- --
-- 348 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 349 Ir 2 1 Ph Iq2 Ph Iq2 --
-- -- -- 350 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 351 Ir 2 1 Ph Iq2 Ph
Iq2 -- -- -- -- 352 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 353 Ir 2 1 Ph
Iq2 Ph Iq2 -- -- -- -- 354 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 355 Ir
2 1 Ph Iq2 Ph Iq2 -- -- -- -- 356 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- --
357 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 358 Ir 2 1 Ph Iq2 Ph Iq2 -- --
-- -- 359 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 360 Ir 2 1 Ph Iq2 Ph Iq2
-- -- -- -- 361 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 362 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 363 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 364 Ir 2 1 Ph
Iq2 Ph Pr -- -- -- -- 365 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 366 Ir 2
1 Ph Iq2 -- -- CH3 CH3 CH3 -- 367 Ir 2 1 Ph Iq2 -- -- C(CH3)3
C(CH3)3 H -- 368 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 369 Ir 2 1 Ph
Iq2 -- -- -- -- -- Pr 370 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 371 Ir 2
1 Ph Iq2 -- -- -- -- -- Iq2 372 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 373
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 374 Ir 2 1 Ph Iq2 Ph Pr -- -- -- --
375 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 376 Ir 2 1 Ph Iq2 -- -- CH3 CH3
CH3 -- 377 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 378 Ir 2 1 Ph
Iq2 -- -- CH3 C4H9 CH3 -- 379 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 380
Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
TABLE-US-00017 TABLE 11-2 A A' B No R1 R2 R3 R4 R1 R2 R3 R4 R5 R6
R7 R8 R9 R10 341 H H C12H25 H H H H H H H H H H H 342 H H C15H31 H
H H H H H H H H H H 343 H H C18H37 H H H H H H H H H H H 344 H H
C20H41 H H H H H H H H H H H 345 H H H H H H CH3 H H H H H H H 346
H H H H H H C2H5 H H H H H H H 347 H H H H H H C3H7 H H H H H H H
348 H H H H H H C4H9 H H H H H H H 349 H H H H H H C(CH3)3 H H H H
H H H 350 H H H H H H C5H11 H H H H H H H 351 H H H H H H C6H13 H H
H H H H H 352 H H H H H H C7H15 H H H H H H H 353 H H H H H H C8H17
H H H H H H H 354 H H H H H H C9H19 H H H H H H H 355 H H H H H H
C10H21 H H H H H H H 356 H H COCH3 H H H C11H23 H H H H H H H 357 H
H H H H H C12H25 H H H H H H H 358 H H C7H15O H H H C15H31 H H H H
H H H 359 H H H H H H C18H37 H H H H H H H 360 H H CN H H H C20H41
H H H H H H H 361 H ##STR00026## H H -- -- -- -- H H H H H H 362 H
##STR00027## H H -- -- -- -- H H H F H H 363 H ##STR00028## H H --
-- -- -- H H H H C6H13 H 364 H ##STR00029## H H H H H H H H H H H H
365 H ##STR00030## H H -- -- -- -- H H H H H H 366 H ##STR00031## H
H -- -- -- -- H H H H H H 367 H ##STR00032## H H -- -- -- -- H H H
H H H 368 H ##STR00033## H H -- -- -- -- H H H H H H 369 H
##STR00034## H H -- -- -- -- H H H H H H 370 H ##STR00035## H H --
-- -- -- H H H H H H 371 H ##STR00036## H H -- -- -- -- H H H H H H
372 H CH3O H H -- -- -- -- H H H H H H 373 H CH3O H H -- -- -- -- H
H H H C6H13 H 374 H CH3O H H H H H H H H H H H H 375 H H CH3O H --
-- -- -- H H H H H H 376 H CH3O H H -- -- -- -- H H H H H H 377 H
CH3O H H -- -- -- -- H H H H H H 378 H CH3O H H -- -- -- -- H H H H
H H 379 H CH3O H H -- -- -- -- H H H H H H 380 H CH3O H H -- -- --
-- H H H H H H B' B'' No R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R9 R10 341
H H H H H H -- -- -- -- -- -- 342 H H H H H H -- -- -- -- -- -- 343
H H H H H H -- -- -- -- -- -- 344 H H H H H H -- -- -- -- -- -- 345
H H H H H H -- -- -- -- -- -- 346 H H H H H H -- -- -- -- -- -- 347
H H H H H H -- -- -- -- -- -- 348 H H H H H H -- -- -- -- -- -- 349
H H H H H H -- -- -- -- -- -- 350 H H H H H H -- -- -- -- -- -- 351
H H H H H H -- -- -- -- -- -- 352 H H H H H H -- -- -- -- -- -- 353
H H H H H H -- -- -- -- -- -- 354 H H H H H H -- -- -- -- -- -- 355
H H H H H H -- -- -- -- -- -- 356 H H H H H H -- -- -- -- -- -- 357
H H H H H H -- -- -- -- -- -- 358 H H H H H H -- -- -- -- -- -- 359
H H H H H H -- -- -- -- -- -- 360 H H H H H H -- -- -- -- -- -- 361
-- -- -- -- -- -- -- -- -- -- -- -- 362 -- -- -- -- -- -- -- -- --
-- -- -- 363 -- -- -- -- -- -- -- -- -- -- -- -- 364 H H H H -- --
-- -- -- -- -- -- 365 -- -- -- -- -- -- -- -- -- -- -- -- 366 -- --
-- -- -- -- -- -- -- -- -- -- 367 -- -- -- -- -- -- -- -- -- -- --
-- 368 -- -- -- -- -- -- -- -- -- -- -- -- 369 -- -- -- -- -- -- H
H H H -- -- 370 -- -- -- -- -- -- H H C4H9 H -- -- 371 -- -- -- --
-- -- H H H H H H 372 -- -- -- -- -- -- -- -- -- -- -- -- 373 -- --
-- -- -- -- -- -- -- -- -- -- 374 H H H H -- -- -- -- -- -- -- --
375 -- -- -- -- -- -- -- -- -- -- -- -- 376 -- -- -- -- -- -- -- --
-- -- -- -- 377 -- -- -- -- -- -- -- -- -- -- -- -- 378 -- -- -- --
-- -- -- -- -- -- -- -- 379 -- -- -- -- -- -- -- -- -- -- -- -- 380
-- -- -- -- -- -- H H C4H9 H -- --
TABLE-US-00018 TABLE 12-1 (Continued to Table 12-2) No M m n A B A
B E G J B 381 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 382 Ir 3 0 Ph Iq2 --
-- -- -- -- -- 383 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 384 Ir 3 0 Ph
Iq2 -- -- -- -- -- -- 385 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 386 Ir 2
1 Ph Iq2 -- -- CH3 CH3 H -- 387 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 --
388 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 389 Ir 2 1 Ph Iq2 --
-- CH3 C4H9 CH3 -- 390 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 391 Ir 2 1
Ph Iq2 -- -- -- -- -- Pr 392 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 393
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 394 Ir 3 0 Ph Iq2 -- -- -- -- -- --
395 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 396 Ir 2 1 Ph Iq2 -- -- CH3 CH3
H -- 397 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 399 Ir 2 1 Ph Iq2 -- --
CH3 C4H9 CH3 -- 400 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 401 Ir 2 1 Ph
Iq2 -- -- -- -- -- Pr 402 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 403 Ir 3
0 Ph Iq2 -- -- -- -- -- -- 404 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 405
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 406 Ir 3 0 Ph Iq2 -- -- -- -- -- --
407 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 408 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 409 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 410 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 411 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 412 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 413 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 414 Ir 3 0
Ph Iq2 -- -- -- -- -- -- 415 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 416 Ir
3 0 Ph Iq2 -- -- -- -- -- -- 417 Ir 2 1 Ph Iq2 Ph Pr -- -- -- --
418 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 419 Ir 2 1 Ph Iq2 -- -- -- --
-- Pr 420 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2
TABLE-US-00019 TABLE 12-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 381 H CH3O H H --
-- -- -- H H H H H H -- -- -- -- H H H H H H 382 H C2H5O H H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 383 H C2H5O H H --
-- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 384 H C2H5O H H
-- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 385 H
C2H5O H H H H H H H H H H H H H H H H -- -- -- -- -- -- 386 H C2H5O
H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 387 H
C2H5O H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 388
H C2H5O H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- --
389 H C2H5O H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- --
-- 390 H C2H5O H H -- -- -- -- H H H H H H -- -- -- -- H H H H --
-- 391 H C2H5O H H -- -- -- -- H H H H H H -- -- -- -- H H C4H9 H
-- -- 392 H C2H5O H H -- -- -- -- H H H H H H -- -- -- -- H H H H H
H 393 H C6H13O H H -- -- -- -- H H H F H H -- -- -- -- -- -- -- --
-- -- 394 H C6H13O H H -- -- -- -- H H H H C6H13 H -- -- -- -- --
-- -- -- -- -- 395 H C6H13O H H H H H H H H H H H H H H H H -- --
-- -- -- -- 396 H C6H13O H H -- -- -- -- H H H H H H -- -- -- -- --
-- -- -- -- -- 397 H C6H13O H H -- -- -- -- H H H H H H -- -- -- --
-- -- -- -- -- -- 399 H C6H13O H H -- -- -- -- H H H H H H -- -- --
-- -- -- -- -- -- -- 400 H C6H13O H H -- -- -- -- H H H H H H -- --
-- -- H H H H -- -- 401 H C6H13O H H -- -- -- -- H H H H H H -- --
-- -- H H C4H9 H -- -- 402 H C6H13O H H -- -- -- -- H H H H H H --
-- -- -- H H H H H H 403 H C7H15O H H -- -- -- -- H H H H H H -- --
-- -- -- -- -- -- -- -- 404 H C7H15O H H -- -- -- -- H H H F H H --
-- -- -- -- -- -- -- -- -- 405 H C7H15O H H -- -- -- -- H H H H
C6H13 H -- -- -- -- -- -- -- -- -- -- 406 H (CH3)3CO H H -- -- --
-- H H H H H H -- -- -- -- -- -- -- -- -- -- 407 H C5H11O H H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 408 H CF3O H H --
-- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 409 H CF3O H H
-- -- -- -- H H H H F H -- -- -- -- -- -- -- -- -- -- 410 H CF3O H
H -- -- -- -- H H H CF3 H H -- -- -- -- -- -- -- -- -- -- 411 H
CF3O H H -- -- -- -- H H H H CF3 H -- -- -- -- -- -- -- -- -- --
412 H C7H15O H H -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- --
-- 413 H C7H15O H H -- -- -- -- H H H H H H -- -- -- -- H H H H H H
414 H (C4H9)3Si H H -- -- -- -- H H H H H H -- -- -- -- -- -- -- --
-- -- 415 H C12H25O H H -- -- -- -- H H H F H H -- -- -- -- -- --
-- -- -- -- 416 H C12H25O H H -- -- -- -- H H H H C6H13 H -- -- --
-- -- -- -- -- -- -- 417 H C12H25O H H H H H H H H H H H H H H H H
-- -- -- -- -- -- 418 H (CH3)3Si H H -- -- -- -- H H H H H H -- --
-- -- -- -- -- -- -- -- 419 H C18H37O H H -- -- -- -- H H H H H H
-- -- -- -- H H C4H9 H -- -- 420 H C18H37O H H -- -- -- -- H H H H
H H -- -- -- -- H H H H H H
TABLE-US-00020 TABLE 13-1 (continued to Table 13-2) No M m n A B A'
B' E G J B'' 421 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 422 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 423 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 424 Ir 2 1 Ph
Iq2 Ph Pr -- -- -- -- 425 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 426 Ir 2
1 Ph Iq2 -- -- CH3 CH3 CH3 -- 427 Ir 2 1 Ph Iq2 -- -- C(CH3)3
C(CH3)3 H -- 428 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 429 Ir 2 1 Ph
Iq2 -- -- -- -- -- Pr 430 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 431 Ir 2
1 Ph Iq2 -- -- -- -- -- Iq2 432 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 433
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 434 Ir 3 0 Ph Iq2 -- -- -- -- -- --
435 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 436 Ir 2 1 Ph Iq2 -- -- CH3 CH3
H -- 437 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 438 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H -- 439 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 440 Ir
2 1 Ph Iq2 -- -- -- -- -- Pr 441 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
442 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 443 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 444 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 445 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 446 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 447 Ir 2 1 Ph Iq2
-- -- CH3 CH3 H -- 448 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 449 Ir 2
1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 450 Ir 2 1 Ph Iq2 -- -- CH3
C4H9 CH3 -- 451 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 452 Ir 2 1 Ph Iq2
-- -- -- -- -- Pr 453 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 454 Ir 3 0
Ph Iq2 -- -- -- -- -- -- 455 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 456 Ir
2 1 Ph Iq2 Ph Pr -- -- -- -- 457 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H --
458 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 459 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H --
TABLE-US-00021 TABLE 13-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 421 F H F H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 422 F H F H -- --
-- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 423 F H F H -- --
-- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 424 F H F H H H
H H H H H H H H H H H H -- -- -- -- -- -- 425 F H F H -- -- -- -- H
H H H H H -- -- -- -- -- -- -- -- -- -- 426 F H F H -- -- -- -- H H
H H H H -- -- -- -- -- -- -- -- -- -- 427 F H F H -- -- -- -- H H H
H H H -- -- -- -- -- -- -- -- -- -- 428 F H F H -- -- -- -- H H H H
H H -- -- -- -- -- -- -- -- -- -- 429 F H F H -- -- -- -- H H H H H
H -- -- -- -- H H H H -- -- 430 F H F H -- -- -- -- H H H H H H --
-- -- -- H H C4H9 H -- -- 431 F H F H -- -- -- -- H H H H F H -- --
-- -- H H H H H H 432 H F H F -- -- -- -- H H H H F H -- -- -- --
-- -- -- -- -- -- 433 H F H F -- -- -- -- H H H F F H -- -- -- --
-- -- -- -- -- -- 434 H F H F -- -- -- -- H H H H C6H13 H -- -- --
-- -- -- -- -- -- -- 435 H F H F H H H H H H H H H H H H H H -- --
-- -- -- -- 436 H F H F -- -- -- -- H H H H H H -- -- -- -- -- --
-- -- -- -- 437 H F H F -- -- -- -- H H H H H H -- -- -- -- -- --
-- -- -- -- 438 H F H F -- -- -- -- H H H H H H -- -- -- -- -- --
-- -- -- -- 439 H F H F -- -- -- -- H H H H H H -- -- -- -- -- --
-- -- -- -- 440 H F H F -- -- -- -- H H H H H H -- -- -- -- H H H H
-- -- 441 H F H F -- -- -- -- H H H H H H -- -- -- -- H H C4H9 H --
-- 442 H F H F -- -- -- -- H H H H H H -- -- -- -- H H H H H H 443
F F F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 444 F
F F F -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 445 F F
F F -- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 446 F
F F F H H H H H H H H H H H H H H -- -- -- -- -- -- 447 F F F F --
-- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 448 F F F F --
-- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 449 F F F F --
-- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 450 F F F F --
-- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 451 F F F F --
-- -- -- H H H H H H -- -- -- -- H H H H -- -- 452 F F F F -- -- --
-- H H H H H H -- -- -- -- H H C4H9 H -- -- 453 F F F F -- -- -- --
H H H H H H -- -- -- -- H H H H H H 454 F F F F -- -- -- -- F F F F
F F -- -- -- -- -- -- -- -- -- -- 455 F F F F -- -- -- -- F F F F
C6H13 F -- -- -- -- -- -- -- -- -- -- 456 F F F F H H H H F F F F F
F H H H H -- -- -- -- -- -- 457 F F F F -- -- -- -- F F F F F F --
-- -- -- -- -- -- -- -- -- 458 F F F F -- -- -- -- F F F F F F --
-- -- -- -- -- -- -- -- -- 459 F F F F -- -- -- -- F F F F F F --
-- -- -- -- -- -- -- -- --
TABLE-US-00022 TABLE 14-1A (continued to Table 14-2A) No M m n A B
A' B' E G J B'' 460 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 461 Ir 2 1
Ph Iq2 -- -- -- -- -- Pr 462 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 463 Ir
2 1 Ph Iq2 -- -- -- -- -- Iq2 464 Ir 3 0 Ph Iq2 -- -- -- -- -- --
465 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 466 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 467 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 468 Ir 2 1 Ph Iq2 -- --
CH3 CH3 H -- 469 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 470 Ir 2 1 Ph Iq2
Ph Iq2 -- -- -- -- 471 Ir 1 2 Ph Iq2 Ph Iq2 -- -- -- -- 472 Ir 2 1
Ph Iq2 -- -- -- -- -- Pr 473 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 474 Ir
2 1 Ph Iq2 -- -- -- -- -- Iq2 475 Ir 3 0 Ph Iq2 -- -- -- -- -- --
476 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 477 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 478 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 479 Ir 2 1 Ph Iq2 Ph Iq2
-- -- -- -- 480 Ir 2 1 Ph Iq2 Ph Iq2 -- -- -- -- 481 Ir 3 0 Ph Iq2
-- -- -- -- -- -- 482 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 483 Ir 2
1 Ph Iq2 Ph Iq2 -- -- -- -- 484 Ir 1 2 Ph Iq2 Ph Iq2 -- -- -- --
485 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2
TABLE-US-00023 TABLE 14-1B (continued to Table 14-2B) No M m n A B
A' B' E G J B'' 486 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 487 Ir 3 0 Ph
Iq2 -- -- -- -- -- -- 488 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 489 Ir 2
1 Ph Iq2 Ph Pr -- -- -- -- 490 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 491
Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 492 Ir 2 1 Ph Iq2 -- -- C(CH3)3
C(CH3)3 H -- 493 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 494 Ir 2 1 Ph
Iq2 -- -- -- -- -- Pr 495 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 496 Ir 2
1 Ph Iq2 -- -- -- -- -- Iq2 497 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 498
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 499 Ir 3 0 Ph Iq2 -- -- -- -- -- --
500 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 501 Ir 2 1 Ph Iq2 -- -- CH3 CH3
H -- 502 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 503 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H -- 504 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 505 Ir
2 1 Ph Iq2 -- -- -- -- -- Pr 506 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
507 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 508 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 509 Ir 3 0 Ph Iq2 -- -- -- -- -- --
TABLE-US-00024 TABLE 14-2A A A' B No R1 R2 R3 R4 R1 R2 R3 R4 R5 R6
R7 R8 R9 R10 460 F F F F -- -- -- -- F F F F F F 461 F F F F -- --
-- -- F F F F F F 462 F F F F -- -- -- -- F F F F F F 463 F F F F
-- -- -- -- F F F F F F 464 H C2F5 H H -- -- -- -- H H H H H H 465
H C2F5 H H -- -- -- -- H H H F H H 466 H C3F7 H H -- -- -- -- H H H
H C6H13 H 467 H C3F7 H H H H H H H H H H H H 468 H C4F9 H H -- --
-- -- H H H H H H 469 H C3F7CH2CH2O H H -- -- -- -- H H H H H H 470
H C3F7CH2CH2O H H H H H H H H H H H H 471 H C3F7CH2CH2O H H H H H H
H H H H H H 472 H C5F11 H H -- -- -- -- H H H H H H 473 H C2F5 H H
-- -- -- -- H H H H H H 474 H C3F7 H H -- -- -- -- H H H H H H 475
H C6F13 H H -- -- -- -- H H H H H H 476 H C6F13 H H -- -- -- -- H H
H CF3 H H 477 H C6F13 H H -- -- -- -- H H H H CF3 H 478 H C6F13 H H
-- -- -- -- H H H H F H 479 H C6F13 H H H H H H H H H H F H 480 H H
H H H C6F13 H H H H H H H H 481 H C6F13CH2O H H -- -- -- -- H H H H
H H 482 H C18F37 H H -- -- -- -- H H H H H H 483 H C6F13CH2O H H H
H H H H H H H H H 484 H C6F13CH2O H H H H H H H H H H H H 485 H
C20F41 H H -- -- -- -- H H H H H H B' B'' No R5 R6 R7 R8 R9 R10 R5
R6 R7 R8 R9 R10 460 -- -- -- -- -- -- -- -- -- -- -- -- 461 -- --
-- -- -- -- H H H H -- -- 462 -- -- -- -- -- -- H H C4H9 H -- --
463 -- -- -- -- -- -- H H H H H H 464 -- -- -- -- -- -- -- -- -- --
-- -- 465 -- -- -- -- -- -- -- -- -- -- -- -- 466 -- -- -- -- -- --
-- -- -- -- -- -- 467 H H H H -- -- -- -- -- -- -- -- 468 -- -- --
-- -- -- -- -- -- -- -- -- 469 -- -- -- -- -- -- -- -- -- -- -- --
470 H H H H H H -- -- -- -- -- -- 471 H H H H H H -- -- -- -- -- --
472 -- -- -- -- -- -- H CH3 H H -- -- 473 -- -- -- -- -- -- H H
C4H9 H -- -- 474 -- -- -- -- -- -- H H H H H H 475 -- -- -- -- --
-- -- -- -- -- -- -- 476 -- -- -- -- -- -- -- -- -- -- -- -- 477 --
-- -- -- -- -- -- -- -- -- -- -- 478 -- -- -- -- -- -- -- -- -- --
-- -- 479 H H H H H H -- -- -- -- -- -- 480 H H H H H H -- -- -- --
-- -- 481 -- -- -- -- -- -- -- -- -- -- -- -- 482 -- -- -- -- -- --
-- -- -- -- -- -- 483 H H H H H H -- -- -- -- -- -- 484 H H H H H H
-- -- -- -- -- -- 485 -- -- -- -- -- -- H H H H H H
TABLE-US-00025 TABLE 14-2B A A' B No R1 R2 R3 R4 R1 R2 R3 R4 R5 R6
R7 R8 R9 R10 486 H ##STR00037## H H -- -- -- -- H H H H H H 487 H
##STR00038## H H -- -- -- -- H H H F H H 488 H ##STR00039## H H --
-- -- -- H H H H C6H13 H 489 H ##STR00040## H H H H H H H H H H H H
490 H ##STR00041## H H -- -- -- -- H H H H H H 491 H ##STR00042## H
H -- -- -- -- H H H H H H 492 H ##STR00043## H H -- -- -- -- H H H
H H H 493 H ##STR00044## H H -- -- -- -- H H H H H H 494 H
##STR00045## H H -- -- -- -- H H H H H H 495 H ##STR00046## H H --
-- -- -- H H H H H H 496 H ##STR00047## CH3 H -- -- -- -- H H H H H
H 497 H H F F -- -- -- -- H H H H H H 498 H H F F -- -- -- -- H H H
F H H 499 H H F F -- -- -- -- H H H H C6H13 H 500 H H F F H H H H H
H H H H H 501 H H F F -- -- -- -- H H H H H H 502 H H F F -- -- --
-- H H H H H H 503 H H F F -- -- -- -- H H H H H H 504 H H F F --
-- -- -- H H H H H H 505 H H F F -- -- -- -- H H H H H H 506 H H F
F -- -- -- -- H H H H H H 507 H H F F -- -- -- -- H H H H H H 508 H
CH3 F F -- -- -- -- H H H CF3 H H 509 H CH3 F F -- -- -- -- H H H F
H H B' B'' No R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R9 R10 486 -- -- -- --
-- -- -- -- -- -- -- -- 487 -- -- -- -- -- -- -- -- -- -- -- -- 488
-- -- -- -- -- -- -- -- -- -- -- -- 489 H H H H -- -- -- -- -- --
-- -- 490 -- -- -- -- -- -- -- -- -- -- -- -- 491 -- -- -- -- -- --
-- -- -- -- -- -- 492 -- -- -- -- -- -- -- -- -- -- -- -- 493 -- --
-- -- -- -- -- -- -- -- -- -- 494 -- -- -- -- -- -- H H H H -- --
495 -- -- -- -- -- -- H H C2H5 H -- -- 496 -- -- -- -- -- -- H H H
H H H 497 -- -- -- -- -- -- -- -- -- -- -- -- 498 -- -- -- -- -- --
-- -- -- -- -- -- 499 -- -- -- -- -- -- -- -- -- -- -- -- 500 H H H
H -- -- -- -- -- -- -- -- 501 -- -- -- -- -- -- -- -- -- -- -- --
502 -- -- -- -- -- -- -- -- -- -- -- -- 503 -- -- -- -- -- -- -- --
-- -- -- -- 504 -- -- -- -- -- -- -- -- -- -- -- -- 505 -- -- -- --
-- -- H H H H -- -- 506 -- -- -- -- -- -- H H C4H9 H -- -- 507 --
-- -- -- -- -- H H H H H H 508 -- -- -- -- -- -- -- -- -- -- -- --
509 -- -- -- -- -- -- -- -- -- -- -- --
TABLE-US-00026 TABLE 15-1 (continued to Table 15-2) No M m n A B A'
B' E G J B'' 510 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 511 Ir 2 1 Ph Iq2
Ph Pr -- -- -- -- 512 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 513 Ir 2 1
Ph Iq2 -- -- CH3 CH3 CH3 -- 514 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3
H -- 515 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 516 Ir 2 1 Ph Iq2 --
-- -- -- -- Pr 517 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 518 Ir 2 1 Ph
Iq2 -- -- -- -- -- Iq2 519 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 520 Ir 3
0 Ph Iq2 -- -- -- -- -- -- 521 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 522
Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 523 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H
-- 524 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 525 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H -- 526 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 527 Ir
2 1 Ph Iq2 -- -- -- -- -- Pr 528 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
529 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 530 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 531 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 532 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 533 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 534 Ir 2 1 Ph Iq2
-- -- CH3 CH3 H -- 535 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 536 Ir 2
1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 537 Ir 2 1 Ph Iq2 -- -- CH3
C4H9 CH3 -- 538 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 539 Ir 2 1 Ph Iq2
-- -- -- -- -- Pr 540 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 541 Ir 3 0
Ph Iq2 -- -- -- -- -- -- 542 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 543 Ir
3 0 Ph Iq2 -- -- -- -- -- -- 544 Ir 2 1 Ph Iq2 Ph Pr -- -- -- --
545 Ir 2 1 Ph Iq2 -- -- CH3 CH3 F -- 546 Ir 2 1 Ph Iq2 -- -- CH3
CH3 CH3 -- 547 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 548 Ir 2 1
Ph Iq2 -- -- CH3 C4H9 CH3 -- 549 Ir 2 1 Ph Iq2 -- -- -- -- --
Pr
TABLE-US-00027 TABLE 15-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 510 H CH3 F F --
-- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 511 H CH3 F
F H H H H H H H H H H H H H H -- -- -- -- -- -- 512 H CH3 F F -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 513 H CH3 F F -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 514 H CH3 F F -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 515 H CH3 F F -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 516 H CH3 F F -- --
-- -- H H H H H H -- -- -- -- H H H H -- -- 517 H CH3 F F -- -- --
-- H H H H H H -- -- -- -- H H C4H9 H -- -- 518 H CH3 F F -- -- --
-- H H H H H H -- -- -- -- H H H H H H 519 H C2H5 F F -- -- -- -- H
H H H H H -- -- -- -- -- -- -- -- -- -- 520 H C2H5 F F -- -- -- --
H H H F H H -- -- -- -- -- -- -- -- -- -- 521 H C2H5 F F -- -- --
-- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 522 H C2H5 F F H H
H H H H H H H H H H H H -- -- -- -- -- -- 523 H C2H5 F F -- -- --
-- H H H H H H -- -- -- -- -- -- -- -- -- -- 524 H C2H5 F F -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 525 H C2H5 F F --
-- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 526 H C3H7 F F
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 527 H C3H7 F
F -- -- -- -- H H H H H H -- -- -- -- H H H H -- -- 528 H C3H7 F F
-- -- -- -- H H H H H H -- -- -- -- H H C4H9 H -- -- 529 H C3H7 F F
-- -- -- -- H H H H H H -- -- -- -- H H H H H H 530 H C4H9 F F --
-- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 531 H C4H9 F F
-- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 532 H C4H9 F
F -- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 533 H
C4H9 F F H H H H H H H H H H H H H H -- -- -- -- -- -- 534 H C4H9 F
F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 535 H C4H9
F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 536 H
C4H9 F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 537
H C4H9 F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- --
538 H C4H9 F F -- -- -- -- H H H H H H -- -- -- -- H H H H -- --
539 H C4H9 F F -- -- -- -- H H H H H H -- -- -- -- H H CH3 H -- --
540 H C4H9 F F -- -- -- -- H H H H H H -- -- -- -- H H H H H H 541
H C(CH3)3 F F -- -- -- -- H H H CF3 H H -- -- -- -- -- -- -- -- --
-- 542 H C(CH3)3 F F -- -- -- -- H H H F H H -- -- -- -- -- -- --
-- -- -- 543 H C(CH3)3 F F -- -- -- -- H H H H C6H13 H -- -- -- --
-- -- -- -- -- -- 544 H C(CH3)3 F F H H H H H H H H H H H H H H --
-- -- -- -- -- 545 H C5H11 F F -- -- -- -- H H H H H H -- -- -- --
-- -- -- -- -- -- 546 H C5H11 F F -- -- -- -- H H H H H H -- -- --
-- -- -- -- -- -- -- 547 H C5H11 F F -- -- -- -- H H H H H H -- --
-- -- -- -- -- -- -- -- 548 H C5H11 F F -- -- -- -- H H H H H H --
-- -- -- -- -- -- -- -- -- 549 H C5H11 F F -- -- -- -- H H H H H H
-- -- -- -- H H H H -- --
TABLE-US-00028 TABLE 16-1 (continued to Table 16-2) No M m n A B A'
B' E G J B'' 550 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 551 Ir 2 1 Ph Iq2
-- -- -- -- -- Iq2 552 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 553 Ir 3 0
Ph Iq2 -- -- -- -- -- -- 554 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 555 Ir
2 1 Ph Iq2 Ph Pr -- -- -- -- 556 Ir 2 1 Ph Iq2 -- -- CF3 CF3 H --
557 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 558 Ir 2 1 Ph Iq2 -- --
C(CH3)3 C(CH3)3 H -- 559 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3 -- 560 Ir
2 1 Ph Iq2 -- -- -- -- -- Pr 561 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
562 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 563 Ir 3 0 Ph Iq2 -- -- -- --
-- -- 564 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 565 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 566 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 567 Ir 2 1 Ph Iq2
-- -- CH3 CH3 H -- 568 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 569 Ir 2
1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 570 Ir 2 1 Ph Iq2 -- -- CH3
C4H9 CH3 -- 571 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 572 Ir 2 1 Ph Iq2
-- -- -- -- -- Pr 573 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 574 Ir 3 0
Ph Iq2 -- -- -- -- -- -- 575 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 576 Ir
3 0 Ph Iq2 -- -- -- -- -- -- 577 Ir 2 1 Ph Iq2 Ph Pr -- -- -- --
578 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H -- 579 Ir 2 1 Ph Iq2 -- -- CH3
CH3 CH3 -- 580 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C(CH3)3 H -- 581 Ir 2 1
Ph Iq2 -- -- CH3 C4H9 CH3 -- 582 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr
583 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 584 Ir 2 1 Ph Iq2 -- -- -- --
-- Iq2 585 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 586 Ir 3 0 Ph Iq2 -- --
-- -- -- -- 587 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 588 Ir 2 1 Ph Iq2
Ph Pr -- -- -- -- 589 Ir 2 1 Ph Iq2 -- -- CH3 CH3 H --
TABLE-US-00029 TABLE 16-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 550 H C6H13 F F
-- -- -- -- H H H H H H -- -- -- -- H H C4H9 H -- -- 551 H C6H13 F
F -- -- -- -- H H H H H H -- -- -- -- H H H H H H 552 H C6H13 F F
-- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 553 H C6H13 F
F -- -- -- -- H H H F H H -- -- -- -- -- -- -- -- -- -- 554 H C6H13
F F -- -- -- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 555 H
C6H13 F F H H H H H H H H H H H H H H -- -- -- -- -- -- 556 H C6H13
F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 557 H
C6H13 F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 558
H C7H15 F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- -- --
559 H C7H15 F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- -- --
-- 560 H C7H15 F F -- -- -- -- H H H H H H -- -- -- -- H H H H --
-- 561 H C8H17 F F -- -- -- -- H H H H H H -- -- -- -- H H C4H9 H
-- -- 562 H C8H17 F F -- -- -- -- H H H H H H -- -- -- -- H H H H H
H 563 H C8H17 F F -- -- -- -- H H H H H H -- -- -- -- -- -- -- --
-- -- 564 H C9H19 F F -- -- -- -- H H H F H H -- -- -- -- -- -- --
-- -- -- 565 H C9H19 F F -- -- -- -- H H H H C6H13 H -- -- -- -- --
-- -- -- -- -- 566 H C10H21 F F H H H H H H H H H H H H H H -- --
-- -- -- -- 567 H C10H21 F F -- -- -- -- H H H H H H -- -- -- -- --
-- -- -- -- -- 568 H C11H23 F F -- -- -- -- H H H H H H -- -- -- --
-- -- -- -- -- -- 569 H C12H25 F F -- -- -- -- H H H H H H -- -- --
-- -- -- -- -- -- -- 570 H C13H27 F F -- -- -- -- H H H H H H -- --
-- -- -- -- -- -- -- -- 571 H C14H29 F F -- -- -- -- H H H H H H --
-- -- -- H H H H -- -- 572 H C15H31 F F -- -- -- -- H H H H H H --
-- -- -- H H C4H9 H -- -- 573 H C15H31 F F -- -- -- -- H H H H H H
-- -- -- -- H H H H H H 574 H C16H33 F F -- -- -- -- H H H H H H --
-- -- -- -- -- -- -- -- -- 575 H C17H35 F F -- -- -- -- H H H F H H
-- -- -- -- -- -- -- -- -- -- 576 H C17H35 F F -- -- -- -- H H H H
C6H13 H -- -- -- -- -- -- -- -- -- -- 577 H C17H35 F F H H H H H H
H H H H H H H H -- -- -- -- -- -- 578 H C17H35 F F -- -- -- -- H H
H H H H -- -- -- -- -- -- -- -- -- -- 579 H C17H35 F F -- -- -- --
H H H H H H -- -- -- -- -- -- -- -- -- -- 580 H C18H37 F F -- -- --
-- H H H H H H -- -- -- -- -- -- -- -- -- -- 581 H C18H37 F F -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 582 H C18H37 F F --
-- -- -- H H H H H H -- -- -- -- H H H H -- -- 583 H C19H39 F F --
-- -- -- H H H H H H -- -- -- -- H H C2H5 H -- -- 584 H C20H41 F F
-- -- -- -- H H H H H H -- -- -- -- H H H H H H 585 F F F H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 586 F F F H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 587 F F F H -- --
-- -- H H H H C6H13 H -- -- -- -- -- -- -- -- -- -- 588 F F F H H H
H H H H H H H H H H H H -- -- -- -- -- -- 589 F F F H -- -- -- -- H
H H H H H -- -- -- -- -- -- -- -- -- --
TABLE-US-00030 TABLE 17-1 (continued to Table 17-2) No M m n A B A'
B' E G J B'' 590 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 -- 591 Ir 2 1 Ph
Iq2 -- -- C(CH3)3 C(CH3)3 H -- 592 Ir 2 1 Ph Iq2 -- -- CH3 C4H9 CH3
-- 593 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 594 Ir 2 1 Ph Iq2 -- -- --
-- -- Pr 595 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 596 Ir 3 0 Ph Iq2 --
-- -- -- -- -- 597 Ir 3 0 Ph Iq2 -- -- -- -- -- -- 598 Ir 3 0 Ph
Iq2 -- -- -- -- -- -- 599 Ir 2 1 Ph Iq2 Ph Pr -- -- -- -- 600 Ir 2
1 Ph Iq2 -- -- CH3 CH3 H -- 601 Ir 2 1 Ph Iq2 -- -- CH3 CH3 CH3 --
602 Ir 2 1 Ph Iq2 -- -- C(CH3)3 C.dbd.(CH3)3 H -- 603 Ir 2 1 Ph Iq2
-- -- CH3 C4H9 CH3 -- 604 Ir 2 1 Ph Iq2 -- -- -- -- -- Pr 605 Ir 2
1 Ph Iq2 -- -- -- -- -- Pr 606 Ir 2 1 Ph Iq2 -- -- -- -- -- Iq2 607
Ir 3 0 Ph Iq2 -- -- -- -- -- -- 608 Ir 3 0 Ph Iq2 -- -- -- -- -- --
609 Ir 3 0 Ph Iq5 -- -- -- -- -- -- 610 Ir 3 0 Ph Iq5 -- -- -- --
-- -- 611 Ir 2 1 Ph Iq5 Ph Pr -- -- -- -- 612 Ir 2 1 Ph Iq5 -- --
CH3 CH3 H -- 613 Ir 2 1 Ph Iq5 -- -- CH3 CH3 CH3 -- 614 Ir 2 1 Ph
Iq5 -- -- C(CH3)3 C(CH3)3 H -- 615 Ir 2 1 Ph Iq5 -- -- CH3 C4H9 CH3
-- 616 Ir 2 1 Ph Iq5 -- -- -- -- -- Pr 617 Ir 2 1 Ph Iq5 -- -- --
-- -- Pr 618 Ir 2 1 Ph Iq5 -- -- -- -- -- Iq2 619 Ir 2 1 Ph Iq2 Ph
Pi -- -- -- --
TABLE-US-00031 TABLE 17-2 A A' B B' B'' No R1 R2 R3 R4 R1 R2 R3 R4
R5 R6 R7 R8 R9 R10 R5 R6 R7 R8 R5 R6 R7 R8 R9 R10 590 F F F H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 591 F F F H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 592 F F F H -- --
-- -- H H H H H H -- -- -- -- -- -- -- -- -- -- 593 F F F H -- --
-- -- H H H H H H -- -- -- -- H H H H -- -- 594 F F F H -- -- -- --
H H H H H H -- -- -- -- H H C4H9 H -- -- 595 F F F H -- -- -- -- H
H H H H H -- -- -- -- H H H H H H 596 F H F H -- -- -- -- H H H H
CF3 H -- -- -- -- -- -- -- -- -- -- 597 F H F H -- -- -- -- H H H F
CF3 H -- -- -- -- -- -- -- -- -- -- 598 F H F H -- -- -- -- H H H H
CF3 H -- -- -- -- -- -- -- -- -- -- 599 F H F H H H H H H H H H CF3
H H H H H -- -- -- -- -- -- 600 F H F H -- -- -- -- H H H H CF3 H
-- -- -- -- -- -- -- -- -- -- 601 F H F H -- -- -- -- H H H H CF3 H
-- -- -- -- -- -- -- -- -- -- 602 F H F H -- -- -- -- H H H H CF3 H
-- -- -- -- -- -- -- -- -- -- 603 F H F H -- -- -- -- H H H H CF3 H
-- -- -- -- -- -- -- -- -- -- 604 F H F H -- -- -- -- H H H H CF3 H
-- -- -- -- H H H H -- -- 605 F H F H -- -- -- -- H H H H CF3 H --
-- -- -- H H CH3 H -- -- 606 F H F H -- -- -- -- H H H H CF3 H --
-- -- -- H H H H H H 607 H CF3 H H -- -- -- -- H H H H H H -- -- --
-- -- -- -- -- -- -- 608 H F H H -- -- -- -- H H H H H H -- -- --
-- -- -- -- -- -- -- 609 H H H H -- -- -- -- -- H H H H H -- -- --
-- -- -- -- -- -- -- 610 H H H H -- -- -- -- -- H H H H H -- -- --
-- -- -- -- -- -- -- 611 H H H H H H H H -- H H H H H H H H H -- --
-- -- -- -- 612 H H H H -- -- -- -- -- H H H H H -- -- -- -- -- --
-- -- -- -- 613 H H H H -- -- -- -- -- H H H H H -- -- -- -- -- --
-- -- -- -- 614 H H H H -- -- -- -- -- H H H H H -- -- -- -- -- --
-- -- -- -- 615 H H H H -- -- -- -- -- H H F H H -- -- -- -- -- --
-- -- -- -- 616 H H H H -- -- -- -- -- H H H H H -- -- -- -- H H H
H -- -- 617 H H H H -- -- -- -- -- H H H H H -- -- -- -- H H CH3 H
-- -- 618 H H H H H H H H -- H H H H H -- -- -- -- H H H H H H 619
H H H H H H H H H H H H H H H H H -- -- -- -- -- -- --
TABLE-US-00032 TABLE 18-1 No M m n A B A' B' B'' 620 Ir 2 1 Ph Iq2
Ph Py1 -- 621 Ir 2 1 Ph Iq2 Ph Py2 -- 622 Ir 2 1 Ph Iq2 Ph Pz --
623 Ir 2 1 Ph Iq2 Ph Qn3 -- 624 Ir 2 1 Ph Iq2 Ph Xa -- 625 Ir 2 1
Ph Iq2 Ph Bz -- 626 Ir 2 1 Ph Iq2 Ph Bo -- 627 Ir 2 1 Ph Iq2 Ph Oz
-- 628 Ir 2 1 Ph Iq2 Ph Sz -- 629 Ir 2 1 Tn4 Iq2 Ph Pr -- 630 Ir 2
1 Ph Iq2 -- -- Pr 631 Ir 2 1 Ph Iq2 -- -- Pr 632 Ir 2 1 Ph Iq2 --
-- Iq2 633 Rh 3 0 Ph Iq2 -- -- -- 634 Rh 3 0 Ph Iq2 -- -- -- 635 Rh
3 0 Ph Iq2 -- -- -- 636 Rh 2 1 Ph Iq2 Ph Pr -- 637 Pt 2 0 Ph Iq2 --
-- -- 638 Pt 2 0 Ph Iq2 -- -- -- 639 Pd 2 0 Ph Iq2 -- -- -- 640 Ir
3 0 Ph Iq6 -- -- -- 641 Ir 3 0 Ph Iq6 -- -- -- 642 Ir 3 0 Ph Iq6 --
-- -- 643 Ir 3 0 Ph Iq6 -- -- -- 644 Ir 3 0 Ph Iq6 -- -- -- 645 Ir
3 0 Ph Iq6 -- -- -- 646 Ir 3 0 Ph Iq6 -- -- -- 647 Ir 3 0 Ph Iq6 --
-- -- 648 Ir 3 0 Ph Iq6 -- -- -- 649 Ir 3 0 Ph Iq6 -- -- -- 650 Ir
3 0 Ph Iq7 -- -- -- 651 Ir 3 0 Ph Iq7 -- -- -- 652 Ir 3 0 Ph Iq7 --
-- -- 653 Ir 3 0 Ph Iq7 -- -- -- 654 Ir 3 0 Ph Iq7 -- -- -- 655 Ir
3 0 Ph Iq7 -- -- -- 656 Ir 3 0 Ph Iq7 -- -- -- 657 Ir 3 0 Ph Iq7 --
-- -- 658 Ir 3 0 Ph Iq7 -- -- -- 659 Ir 3 0 Ph Iq7 -- -- --
TABLE-US-00033 TABLE 18-2 A A' B No R1 R2 R3 R4 R1 R2 R3 R4 R5 R6
R7 R8 620 H H H H H H H H H H H H 621 H H H H H H H H H H H H 622 H
CF3 H H H H H H H H H H 623 H H H H H H H H H H H H 624 H H H H H H
H H H H H H 625 H H H H H H H H H H H H 626 H H H H H H H H H H H H
627 H H H H H H H H H H H H 628 H H H H H H H H H H H H 629 H H --
-- H H H H H H H H 630 H H H H -- -- -- -- H H H H 631 H H H H --
-- -- -- H H H H 632 H H H H -- -- -- -- H H H H 633 F H F H -- --
-- -- H H H F 634 F H F H -- -- -- -- H H H F 635 F H F H -- -- --
-- H H H F 636 F H F H H H H H H H H F 637 F H F H -- -- -- -- H H
H H 638 F H F H -- -- -- -- H H H H 639 F H F H -- -- -- -- H H H H
640 H H H H -- -- -- -- H H H -- 641 H H F H -- -- -- -- H H H --
642 F H F H -- -- -- -- H H H -- 643 H CF3 H H -- -- -- -- H H H --
644 H CH3 H H -- -- -- -- H H H -- 645 H C4H9 H H -- -- -- -- H H H
-- 646 H C3F7 H H -- -- -- -- H H H -- 647 H OC6H13 C3H7 H -- -- --
-- H H H -- 648 F F F H -- -- -- -- H H H -- 649 H OCF3 H H -- --
-- -- H H H -- 650 H H H H -- -- -- -- H H H H 651 H H F H -- -- --
-- H H H H 652 F H F H -- -- -- -- H H H H 653 H CF3 H H -- -- --
-- H H H CF3 654 H CH3 H H -- -- -- -- H H H H 655 H C4H9 H H -- --
-- -- H H H H 656 H C3F7 H H -- -- -- -- H H H H 657 H OC6H13 C3H7
H -- -- -- -- H H H H 658 F F F H -- -- -- -- H H H H 659 H OCF3 H
H -- -- -- -- H H H H B B' B'' No R9 R10 R5 R6 R7 R8 R9 R10 R5 R6
R7 R8 R9 R10 620 H H H H -- H -- -- -- -- -- -- -- -- 621 H H -- H
H H -- -- -- -- -- -- -- -- 622 H H H -- H H -- -- -- -- -- -- --
-- 623 H H H H H H H H -- -- -- -- -- -- 624 H H H -- H H H H -- --
-- -- -- -- 625 H H H H H H -- -- -- -- -- -- -- -- 626 H H H H H H
-- -- -- -- -- -- -- -- 627 H H H H -- -- -- -- -- -- -- -- -- --
628 H H H H -- -- -- -- -- -- -- -- -- -- 629 H H H H H H -- -- --
-- -- -- -- -- 630 H H -- -- -- -- -- -- H H H H -- -- 631 H H --
-- -- -- -- -- H H CH3 H -- -- 632 H H -- -- -- -- -- -- H H H H H
H 633 H H -- -- -- -- -- -- -- -- -- -- -- -- 634 H H -- -- -- --
-- -- -- -- -- -- -- -- 635 H H -- -- -- -- -- -- -- -- -- -- -- --
636 H H H H H H -- -- -- -- -- -- -- -- 637 F H -- -- -- -- -- --
-- -- -- -- -- -- 638 F H -- -- -- -- -- -- -- -- -- -- -- -- 639 F
H -- -- -- -- -- -- -- -- -- -- -- -- 640 H H -- -- -- -- -- -- --
-- -- -- -- -- 641 H H -- -- -- -- -- -- -- -- -- -- -- -- 642 F H
-- -- -- -- -- -- -- -- -- -- -- -- 643 CF3 H -- -- -- -- -- -- --
-- -- -- -- -- 644 H H -- -- -- -- -- -- -- -- -- -- -- -- 645 H H
-- -- -- -- -- -- -- -- -- -- -- -- 646 H H -- -- -- -- -- -- -- --
-- -- -- -- 647 H H -- -- -- -- -- -- -- -- -- -- -- -- 648 CF3 H
-- -- -- -- -- -- -- -- -- -- -- -- 649 H H -- -- -- -- -- -- -- --
-- -- -- -- 650 -- H -- -- -- -- -- -- -- -- -- -- -- -- 651 -- H
-- -- -- -- -- -- -- -- -- -- -- -- 652 -- H -- -- -- -- -- -- --
-- -- -- -- -- 653 -- H -- -- -- -- -- -- -- -- -- -- -- -- 654 --
H -- -- -- -- -- -- -- -- -- -- -- -- 655 -- H -- -- -- -- -- -- --
-- -- -- -- -- 656 -- H -- -- -- -- -- -- -- -- -- -- -- -- 657 --
H -- -- -- -- -- -- -- -- -- -- -- -- 658 -- H -- -- -- -- -- -- --
-- -- -- -- -- 659 -- H -- -- -- -- -- -- -- -- -- -- -- --
TABLE-US-00034 TABLE 19 A B No M m' A B R1 R2 R3 R4 R5 R6 R7 R8 R9
R10 660 Ir 2 Ph Iq2 H H H H H H H H H H 661 Ir 2 Ph Iq2 H CH3 H H H
H H H H H 662 Ir 2 Ph Iq2 H C2H5 H H H H H H H H 663 Ir 2 Ph Iq2 H
C3H7 H H H H H H H H 664 Ir 2 Ph Iq2 H C4H9 H H H H H H H H 665 Ir
2 Ph Iq2 H C(CH3)3 H H H H H H H H 666 Ir 2 Ph Iq2 H C5H11 H H H H
H H H H 667 Ir 2 Ph Iq2 H C6H13 H H H H H H H H 668 Ir 2 Ph Iq2 H
C7H15 H H H H H H H H 669 Ir 2 Ph Iq2 H C8H17 H H H H H H H H 670
Ir 2 Ph Iq2 H C9H19 H H H H H H H H 671 Ir 2 Ph Iq2 H C10H21 H H H
H H H H H 672 Ir 2 Ph Iq2 H C11H23 H H H H H H H H 673 Ir 2 Ph Iq2
H C12H25 H H H H H H H H 674 Ir 2 Ph Iq2 H C13H27 H H H H H H H H
675 Ir 2 Ph Iq2 H C14H29 H H H H H H H H 676 Ir 2 Ph Iq2 H C15H31 H
H H H H H H H 677 Ir 2 Ph Iq2 H C16H33 H H H H H H H H 678 Ir 2 Ph
Iq2 H C17H35 H H H H H H H H 679 Ir 2 Ph Iq2 H C18H37 H H H H H H H
H 680 Ir 2 Ph Iq2 H C19H39 H H H H H H H H 681 Ir 2 Ph Iq2 H C20H41
H H H H H H H H 682 Ir 2 Ph Iq2 F H H H H H H H H H 683 Ir 2 Ph Iq2
H F H H H H H H H H 684 Ir 2 Ph Iq2 H H F H H H H H H H 685 Ir 2 Ph
Iq2 H H H F H H H H H H 686 Ir 2 Ph Iq2 F H F H H H H H H H 687 Ir
2 Ph Iq2 H F F H H H H H H H 688 Ir 2 Ph Iq2 H F H F H H H H H H
689 Ir 2 Ph Iq2 F F F H H H H H H H
TABLE-US-00035 TABLE 20 A B No M m' A B R1 R2 R3 R4 R5 R6 R7 R8 R9
R10 690 Ir 2 Ph Iq2 F F F F H H H CF3 H H 691 Ir 2 Ph Iq2 H CF3 H H
H H H H CF3 H 692 Ir 2 Ph Iq2 H H CF3 H H H H H CF3 H 693 Ir 2 Ph
Iq2 H H H CF3 H H H H H H 694 Ir 2 Ph Iq2 CF3 H CF3 H H H H H CF3 H
695 Ir 2 Ph Iq2 H CH3 F F H H H H H H 696 Ir 2 Ph Iq2 H C2H5 F F H
H H H F H 697 Ir 2 Ph Iq2 H C3H7 F F H H H H H H 698 Ir 2 Ph Iq2 H
C4H9 F F H H H H F H 699 Ir 2 Ph Iq2 H C5H11 F F H H H H H H 700 Ir
2 Ph Iq2 H C6H13 F F H H H H CF3 H 701 Ir 2 Ph Iq2 H C12H25 F F H H
H H H H 702 Ir 2 Ph Iq2 H C15H31 F F H H H H H H 703 Ir 2 Ph Iq2 H
C20H41 F F H H H H H H 704 Ir 2 Ph Iq2 H H H H H H H F H H 705 Ir 2
Ph Iq2 H H H H H H H H F H 706 Ir 2 Ph Iq2 H H H H H H H CF3 H H
707 Ir 2 Ph Iq2 H H H H H H H H CF3 H 708 Ir 2 Ph Iq2 H H H H F F F
F F F 709 Ir 2 Ph Iq2 F F F F F F F F F F 710 Ir 2 Ph Iq2 H CF3 H H
H H H F H H 711 Ir 2 Ph Iq2 H C2F5 H H H H H H H H 712 Ir 2 Ph Iq2
H C3F7 H H H H H H H H 713 Ir 2 Ph Iq2 H C4F9 H H H H H H CF3 H 714
Ir 2 Ph Iq2 H C5F11 H H H H H H H H 715 Ir 2 Ph Iq2 H C6F13 H H H H
H H H H 716 Ir 2 Ph Iq2 H C7F15 H H H H H H CF3 H 717 Ir 2 Ph Iq2 H
C8F17 H H H H H H H H 718 Ir 2 Ph Iq2 H C10F21 H H H H H H H H 719
Ir 2 Ph Iq2 H C15F31 H H H H H H H H
TABLE-US-00036 TABLE 21 A B No M m' A B R1 R2 R3 R4 R5 R6 R7 R8 R9
R10 720 Ir 2 Ph Iq2 H ##STR00048## H H H H H H H H 721 Ir 2 Ph Iq2
H H CH3 H H H H H H H 722 Ir 2 Ph Iq2 H H ##STR00049## H H H H H H
H 723 Ir 2 Ph Iq2 H H C2H5 H H H H H H H 724 Ir 2 Ph Iq2 H H C3H7 H
H H H H H H 725 Ir 2 Ph Iq2 H H C4H9 H H H H H H H 726 Ir 2 Ph Iq2
H H C(CH3)3 H H H H H H H 727 Ir 2 Ph Iq2 H H C5H11 H H H H H H H
728 Ir 2 Ph Iq2 H H C6H13 H H H H H H H 729 Ir 2 Ph Iq2 H H C7H15 H
H H H H H H 730 Ir 2 Ph Iq2 H H C8H17 H H H H H H H 731 Ir 2 Ph Iq2
H H C9H19 H H H H H H H 732 Ir 2 Ph Iq2 H H C10H21 H H H H H H H
733 Ir 2 Ph Iq2 H H C11H23 H H H H H H H 734 Ir 2 Ph Iq2 H H C12H25
H H H H H H H 735 Ir 2 Ph Iq2 H H C15H31 H H H H H H H 736 Ir 2 Ph
Iq2 H H C18H37 H H H H H H H 737 Ir 2 Ph Iq2 H H C20H41 H H H H H H
H 738 Ir 2 Ph Iq2 H H CH3 H H H H H H H 739 Ir 2 Fl Iq2 H H -- -- H
H H H H H 740 Ir 2 Tn1 Iq2 H H -- -- H H H H H H 741 Ir 2 Tn2 Iq2 H
H -- -- H H H H H H 742 Ir 2 Tn3 Iq2 H H -- -- H H H H H H 743 Ir 2
Tn4 Iq2 H H -- -- H H H H H H 744 Ir 2 Np1 Iq2 H H -- -- H H H H H
H 745 Ir 2 Np2 Iq2 H H -- -- H H H H H H 746 Ir 2 Cn1 Iq2 H H -- --
H H H H H H 747 Ir 2 Cn2 Iq2 H H -- -- H H H H H H 748 Ir 2 Pe Iq2
H H -- -- H H H H H H 749 Ir 2 Qn1 Iq2 H H -- -- H H H H H H 750 Ir
2 Qn2 Iq2 H H -- -- H H H H H H
TABLE-US-00037 TABLE 22 A B No M m' A B R1 R2 R3 R4 R5 R6 R7 R8 R9
R10 751 Ir 2 Cz Iq2 H C2H5 -- -- H H H H H H 752 Ir 2 Ph Iq5 H H
CF3 H -- H H H H H 753 Ir 2 Ph Iq5 H H H CF3 -- H H H H H 754 Ir 2
Ph Iq5 CF3 H CF3 H -- H H H H H 755 Ir 2 Ph Iq5 H H H H -- H H H H
H 756 Ir 2 Ph Iq5 H CH3 F F -- H H H H H 757 Ir 2 Ph Iq5 H C2H5 F F
-- H H H H H 758 Ir 2 Ph Iq5 H C3H7 F F -- H H H H H 759 Ir 2 Ph
Iq5 H C4H9 F F -- H H H H H 760 Ir 2 Ph Iq5 H C5H11 F F -- H H H H
H 761 Ir 2 Ph Iq5 H C6H13 F F -- H H H H H 762 Ir 2 Ph Iq5 H C6F13
H H -- H H H H H 763 Ir 2 Ph Iq6 H H H H H H H -- H H 764 Ir 2 Ph
Iq6 H H F H H H H -- H H 765 Ir 2 Ph Iq6 F H F H H H H -- F H 766
Ir 2 Ph Iq6 H CF3 H H H H H -- CF3 H 767 Ir 2 Ph Iq6 H CH3 H H H H
H -- H H 768 Ir 2 Ph Iq6 H C4H9 H H H H H -- H H 769 Ir 2 Ph Iq6 H
C3F7 H H H H H -- H H 770 Ir 2 Ph Iq6 H OC6H13 C3H7 H H H H -- H H
771 Ir 2 Ph Iq6 F F F H H H H -- CF3 H 772 Ir 2 Ph Iq6 H OCF3 H H H
H H -- H H 773 Ir 2 Ph Iq7 H H H H H H H H -- H 774 Ir 2 Ph Iq7 H H
F H H H H H -- H 775 Ir 2 Ph Iq7 F H F H H H H H -- H 776 Ir 2 Ph
Iq7 H CF3 H H H H H CF3 -- H 777 Ir 2 Ph Iq7 H CH3 H H H H H H -- H
778 Ir 2 Ph Iq7 H C4H9 H H H H H H -- H 779 Ir 2 Ph Iq7 H C3F7 H H
H H H H -- H 780 Ir 2 Ph Iq7 H OC6H13 C3H7 H H H H H -- H 781 Ir 2
Ph Iq7 F F F H H H H F -- H 782 Ir 2 Ph Iq7 H OCF3 H H H H H H --
H
TABLE-US-00038 TABLE 23 A B No M m n A B R1 R2 R3 R4 R5 R6 R7 R8 R9
R10 783 Ir 3 0 Ph Iq8 H H H H H -- H H H H 784 Ir 3 0 Ph Iq8 H H F
H H -- H H H H 785 Ir 3 0 Ph Iq8 F H F H H -- H H F H 786 Ir 3 0 Ph
Iq8 H CF3 H H H -- H H CF3 H 787 Ir 3 0 Ph Iq8 H CH3 H H H -- H H H
H 788 Ir 3 0 Ph Iq8 H C4H9 H H H -- H H H H 789 Ir 3 0 Ph Iq8 H
C3F7 H H H -- H H H H 790 Ir 3 0 Ph Iq8 H OC6H13 C3H7 H H -- H H H
H 791 Ir 3 0 Ph Iq8 F F F H H -- H H CF3 H 792 Ir 3 0 Ph Iq8 H OCF3
H H H -- H H H H 793 Ir 3 0 Ph Iq9 H H H H H H -- H H H 794 Ir 3 0
Ph Iq9 H H F H H H -- H H H 795 Ir 3 0 Ph Iq9 F H F H H H -- H F H
796 Ir 3 0 Ph Iq9 H CF3 H H H H -- H CF3 H 797 Ir 3 0 Ph Iq9 H CH3
H H H H -- H H H 798 Ir 3 0 Ph Iq9 H C4H9 H H H H -- H H H 799 Ir 3
0 Ph Iq9 H C3F7 H H H H -- H H H 800 Ir 3 0 Ph Iq9 H OC6H13 C3H7 H
H H -- H H H 801 Ir 3 0 Ph Iq9 F F F H H H -- H CF3 H 802 Ir 3 0 Ph
Iq9 H OCF3 H H H H -- H H H 803 Ir 3 0 Ph Iq10 H H H H H H H H H --
804 Ir 3 0 Ph Iq10 H H F H H H H H H -- 805 Ir 3 0 Ph Iq10 F H F H
H H H H F -- 806 Ir 3 0 Ph Iq10 H CF3 H H H H H H CF3 -- 807 Ir 3 0
Ph Iq10 H CH3 H H H H H H H -- 808 Ir 3 0 Ph Iq10 H C4H9 H H H H H
H H -- 809 Ir 3 0 Ph Iq10 H C3F7 H H H H H H H -- 810 Ir 3 0 Ph
Iq10 H OC6H13 C3H7 H H H H H H -- 811 Ir 3 0 Ph Iq10 F F F H H H H
H CF3 -- 812 Ir 3 0 Ph Iq10 H OCF3 H H H H H H H --
EXAMPLES
[0159] Hereinbelow, the present invention will be described more
specifically based on Examples.
Examples 1 and 2
[0160] In these Examples, a device (effective display area=3
mm.sup.2) having a device structure including 4 organic layers as
shown in FIG. 1(c) was prepared. An alkali-free glass sheet was
used as a transparent substrate 15 and a 100 nm-thick indium oxide
(ITO) film was formed by sputtering and patterned as a transparent
electrode 14. Further, .alpha.-NPD represented by the
above-mentioned structural formula was vacuum-deposited in a layer
thickness of 40 nm thereon as a hole-transporting layer 13. Then,
as an organic luminescence layer 12, the above-mentioned CBP as a
host material and a prescribed metal coordination compound in an
amount of providing 8 wt. % were co-vacuum deposited in a layer
thickness of 30 nm. Further, as an exciton diffusion-prevention
layer 17, BCP was vacuum-deposited in a thickness of 10 nm. Then,
as an electron-transporting layer 16, the above-mentioned Alq3 was
subjected to resistance heating vacuum deposition at a vacuum of
10.sup.-4 Pa to form an organic film in a thickness of 30 nm.
[0161] On the above, as a lower layer of a metal electrode layer
11, an AlLi alloy film was disposed in a thickness of 15 nm, and a
100 nm-thick Al film was vacuum-deposited thereon to form a
patterned metal electrode 11 disposed opposite to the transparent
electrode 14 and having an electrode area of 3 mm.sup.2.
[0162] As the ligands, Example Compound No. 1 (Example 1) and
Example Compound No. 28 (Example 2) shown in Table 1 were used
respectively.
[0163] The performances of the thus-obtained EL devices were
measured by using a micro-current meter ("4140B", made by
Hewlett-Packard Corp.) for a current-voltage characteristic and
"BM7" (made by Topcon K.K.) for an emission luminance. The devices
using the respective coordination compounds respectively exhibited
a good rectifying characteristic.
[0164] At an applied voltage of 12 volts, the EL devices exhibited
luminances as follows:
[0165] Device of Example 1 (Compound No. 1): 8000 cd/m.sup.2
[0166] Device of Example 2 (Compound No. 28): 3500 cd/m.sup.2
[0167] For examining luminescence characteristics of the Coordinate
Compounds No. 1 and No. 28, the solutions were subjected to
measurement of a luminescence spectrum. More specifically, each
solution having a coordination compound concentration of 10.sup.-4
mol/1 in toluene (or chloroform) was illuminated with excitation
light of around 350 nm to measure a luminescence spectrum by using
a spectral fluorophotometer ("F4500", made by Hitachi K.K.). The
luminescence spectra almost coincided with the spectra from the EL
devices at the time of voltage application, whereby it was
confirmed that the luminescences of the EL devices were emitted
from the coordination compounds. (Refer to Example 7 and 8
described hereinafter.)
Examples 3-5, Comparative Example 1
[0168] Luminescence devices were prepared in the same manner as in
Examples 1 and 2 except for using luminescence materials (Example
Compounds) shown in Table 24 below. In Comparative Example 1, the
above-mentioned Ir(ppy).sub.3 was used as a representative of
conventional luminescence material.
[0169] A current conduction durability test was performed for each
device by applying a DC voltage of 12 volts between the ITO
electrode as the anode and the Al electrode as the cathode to
measure a time within which the luminance was attenuated to a
half.
[0170] The measurement results are shown in Table 24 and the
Example materials exhibited a luminance half-attenuation period
which was clearly longer than the Conventional luminescence
material, thus providing a device having a high durability
attributable to the material of the present invention.
TABLE-US-00039 TABLE 24 Luminescence Luminance half- material
attenuation period Example No. (hours) 3 1 1550 4 24 1100 5 28 1350
Comp. 1 Ir(ppy).sub.3 350
Example 6
[0171] A simple matrix type organic EL device as shown in FIG. 2
was prepared in the following manner.
[0172] On a glass substrate 21 measuring 100 nm-length, 100
mm-width and 1.1 mm-thickness, a ca. 100 nm-thick ITO film was
formed by sputtering and patterned into 100 lines of 100 .mu.m-wide
transparent electrodes 22 (anode side) with a spacing of 40 .mu.m
as simple matrix electrodes. Then, formed layers of identical
organic materials were found under identical conditions as in
Example 1 to form an organic compound layer 23.
[0173] Then, 100 lines of 100 .mu.m-wide Al electrodes 24 were
formed with a spacing of 40 .mu.m by mask vacuum deposition so as
to be perpendicular to the transparent electrodes 22 by vacuum
deposition at a vacuum of 2.7.times.10.sup.-3 Pa. The metal
electrodes (cathode) 24 were formed as a lamination of 10 nm-thick
layer of Al/Li alloy (Li: 1.3 wt. %) and then 150 nm-thick layer of
Al.
[0174] The thus-obtained 100.times.100-simple matrix-type organic
EL device was subjected to a simple matrix drive in a glove box
filled with nitrogen at voltages of 7 volts to 13 volts by using a
scanning signal of 10 volts and data signals of .+-.3 volts. As a
result of an interlaced drive at a frame efficiency of 30 Hz,
respectively, luminescence images could be confirmed.
Example 7
Synthesis of Example Compound No. 1
##STR00050##
[0176] 69.3 g (448 mmol) of isoquinoline N-oxide (made by Tokyo
Kasei) and 225 ml of chloroform were placed and dissolved in a 1
liter-three-necked flask, and under stirring and cooling with ice,
219.6 g (1432 mmol) of phosphorus oxychloride was gradually added
dropwise thereto while the internal temperature was held at
15-20.degree. C. Thereafter, the temperature was raised, and reflux
under stirring was performed for 3 hours. The reaction product was
cooled by standing to room temperature and poured into iced water.
After extraction with ethyl acetate, the organic layer washed with
water until neutrality, and the solvent was removed under a reduced
pressure to provide a dry solid, which was then purified by silica
gel column chromatography (eluent: chloroform/hexane=5/1) to obtain
35.5 g (yield: 44.9%) of 1-chloroisoquinoline white crystal.
##STR00051##
[0177] In a 100 ml-three-necked flask, 3.04 g (24.9 mole) of
phenylboronic acid (made by Tokyo Kasei), 4.0 g of (25.0 mmole) of
1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25
ml of 2M-sodium carbonate aqueous solution were placed and stirred
at room temperature under nitrogen stream, and 0.98 g (0.85 mmole)
of tetrakis(triphenylphosphine)palladium (0) was added thereto.
Thereafter, reflux under stirring was performed for 8 hours under
nitrogen stream. After completion of the reaction, the reaction
product was cooled and extracted by addition of cold water and
toluene. The organic layer was washed with saline water and dried
on magnesium sulfate, followed by removal of the solvent under a
reduced pressure to provide dry solid. The residue was purified by
silica gel column chromatography (eluent: chloroform/methanol=10/1)
to obtain 2.20 g (yield=43.0%) of 1-phenylisoquinoline. FIG. 7
shows a .sup.1H-NMR spectrum of a solution of the compound in heavy
chloroform.
##STR00052##
[0178] In a 100 ml-four-necked flask, 50 ml of glycerol was placed
and heated at 130-140.degree. C. under stirring and bubbling with
nitrogen for 2 hours. Then, the glycerol was cooled by standing
down to 100.degree. C., and 1.03 g (5.02 mmole) of
1-phenylisoquinoline and 0.50 g (1.02 mmole) of iridium (III)
acetylacetonate (made by Strem Chemicals, Inc.) were added,
followed by 7 hours of heating around .+-.210.degree. C. under
stirring and nitrogen stream. The reaction product was cooled to
room temperature and injected into 300 ml of 1N-hydrochloric acid
to form a precipitate, which was filtered out and washed with
water. The precipitate was purified by silica gel column
chromatography with chloroform as the eluent to obtain 0.22 g
(yield=26.8%) of red powdery
tris(1-phenylisoquinoline-C.sup.2,N)iridium (III). According to
MALDI-TOF MS (matrix-assisted laser desorption ionization-time of
fight mass spectroscopy), the compound exhibited M.sup.+ (mass
number of the corresponding cation formed by removal of 1 electron)
of 805.2.
[0179] A solution in heavy chloroform of the compound provided a
.sup.1H-NMR spectrum as shown in FIG. 8. A chloroform solution of
the compound exhibited a luminescence spectrum showing
.lamda.max=619 nm and a quantum yield of 0.66 relative to 1.0 of
Ir(ppy).sub.3.
[0180] An EL device of Example 1 prepared by using the compound
exhibited red luminescence showing .lamda.max=620 nm under voltage
application.
Example 8
Synthesis of Example Compound No. 28
##STR00053##
[0182] In a 100 ml-three-necked flask, 2.91 g (12.2 mmole) of
9,9-dimethylfluorene-2-boronic acid, 2.00 g (12.2=mole) of
1-chloroisoquinoline, 10 ml of toluene, 5 ml of ethanol and 10 ml
of 2M-sodium carbonate aqueous solution were placed and stirred at
room temperature under nitrogen stream, and 0.44 g (0.38 mmole) of
tetrakis(triphenylphosphine)palladium (0) was added thereto.
Thereafter, reflux under stirring was performed for 5 hours under
nitrogen stream. After completion of the reaction, the reaction
product was cooled and extracted by addition of cold water and
toluene. The organic layer was washed with saline water and dried
on magnesium sulfate, followed by removal of the solvent under a
reduced pressure to provide dry solid. The residue was purified by
silica gel column chromatography (eluent: toluene/ethyl
acetate=50/1) to obtain 2.13 g (yield=54.2%) of
1-(9,9-dimethylfluorene-2-yl) isoquinoline.
##STR00054##
[0183] In a 100 ml-four-necked flask, 50 ml of glycerol was placed
and heated at 130-140.degree. C. under stirring and bubbling with
nitrogen for 2 hours. Then, the glycerol was cooled by standing
down to 100.degree. C., and 1.61 g (5.01 mmole) of
1-(9,9-dimethylfluorene-2-yl)isoquinoline and 0.50 g (1.02 mmole)
of iridium (III) acetylacetonate were added, followed by 8 hours of
reflux under stirring and nitrogen stream. The reaction product was
cooled to room temperature and injected into 600 ml of
1N-hydrochloric acid to form a precipitate, which was filtered out
and washed with water. The precipitate was purified by silica gel
column chromatography with chloroform as the eluent to obtain 0.38
g (yield 32.3%) of red powdery
tris[1-(9,9-dimethylfluorene-2-yl)isoquinoline-C.sup.3,N]iridium
(III). According to MALDI-TOF MS, the compound exhibited M.sup.+ of
1153.4.
[0184] A toluene solution of the compound exhibited a luminescence
spectrum showing .lamda.max=648 nm and a quantum yield of 0.66
relative to 1.0 of Ir(ppy).sub.3.
[0185] An EL device of Example 2 prepared by using the compound
exhibited red luminescence showing .lamda.max=650 nm under voltage
application.
Example 9
Synthesis of Example Compound No. 25
##STR00055##
[0187] In a 100 ml-three-necked flask, 4.45 g (25.0 mmole) of
thianaphthene-2-boronic acid (made by Aldrich Chemical Co., Inc.),
4.09 g (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5
ml of ethanol and 25 mol of 2M-sodium carbonate aqueous solution
were placed and stirred at room temperature under nitrogen stream,
and 0.98 g (0.85 mmole) of tetrakis(triphenylphosphine)palladium
(0) was added thereto. Thereafter, reflux under stirring was
performed for 8 hours under nitrogen stream. After completion of
the reaction, the reaction product was cooled and extracted by
addition of cold water and toluene. The organic layer was washed
with saline water and dried on magnesium sulfate, followed by
removal of the solvent under a reduced pressure to provide dry
solid. The residue was purified by silica gel column chromatography
(eluent: chloroform) to obtain 4.20 g (yield=64.3.%) of
1-(thianaphthene-2-yl)isoquinoline.
##STR00056##
[0188] In a 100 ml-four-necked flask, 50 ml of glycerol was placed
and heated at 130-140.degree. C. under stirring and bubbling with
nitrogen for 2 hours. Then, the glycerol was cooled by standing to
100.degree. C., and 1.31 g (5.01 mmole) of
1-(thianaphthene-2-yl)-isoquinoline, and 0.50 g (1.02 mmole) of
iridium (III) acetylacetone, were added, followed by 5 hours of
heating around 210.degree. C. under stirring and nitrogen stream.
The reaction product was cooled to room temperature and poured into
300 ml of 1N-hydrochloric acid to form a precipitate, which was
then filtered out and washed with water. The precipitate was
purified by silica gel column chromatography with chloroform as the
eluent to obtain 0.25 g (yield=25.2%) of red powdery
tris[1-(thianaphthene-2-yl)-isoquinoline-C.sup.3,N]iridium (III).
According to MALDI-TOF MS, M.sup.+ of the compound of 973.1 was
confirmed. A toluene solution of the compound exhibited a
luminescence spectrum showing .lamda.max=686 nm and a quantum yield
of 0.07 relative to 1.0 of Ir(ppy).sub.3.
[0189] An EL device was prepared in the same manner as in Example 1
except for using the compound instead of Compound No. 1 and was
confirmed to emit deep red luminescence under voltage
application.
Example 10
Synthesis of Example Compound No. 24
##STR00057##
[0191] In a 100 ml-three-necked flask, 2.56 g (20.0 mmole) of
2-thiophene-2-boronic acid (made by Aldrich Co.), 3.27 g (20.0
mmole) of 1-chloroisoquinoline, 18 ml of toluene, 9 ml of ethanol
and 18 mol of 2M-sodium carbonate aqueous solution were placed and
stirred at room temperature under nitrogen stream, and 0.72 g (0.62
mmole) of tetrakis(triphenylphosphine)palladium (0) was added
thereto. Thereafter, reflux under stirring was performed for 9
hours under nitrogen stream. After completion of the reaction, the
reaction product was cooled and extracted by addition of cold water
and toluene. The organic layer was washed with saline water and
dried on magnesium sulfate, followed by removal of the solvent
under a reduced pressure to provide dry solid. The residue was
purified by silica gel column chromatography (eluent: chloroform)
to obtain 2.40 g (yield=56.8%) of 1-(2-thienyl)isoquinoline.
##STR00058##
[0192] In a 100 ml-four-necked flask, 50 ml of glycerol was placed
and heated at 130-140.degree. C. under stirring and bubbling with
nitrogen for 2 hours. Then, the glycerol was cooled by standing to
100.degree. C., and 1.05 g (4.97 mmole) of
1-(2-thienyl)isoquinoline, and 0.50 g (1.02 mmole) of iridium (III)
acetylacetone, were added, followed by 8 hours of reflux under
stirring and nitrogen stream. The reaction product was cooled to
room temperature and poured into 600 ml of 1N-hydrochloric acid to
form a precipitate, which was then filtered out and washed with
water. The precipitate was purified by silica gel column
chromatography with chloroform as the eluent to obtain 0.38 g
(yield=45.2%) of red powdery
tris[1-(2-thienyl)isoquinoline-C.sup.3,N]iridium (III). According
to MALDI-TOF MS, M.sup.+ of the compound of 823.1 was confirmed. A
toluene solution of the compound exhibited a luminescence spectrum
showing .lamda.max=642 nm and a quantum yield of 0.43 relative to
1.0 of Ir(ppy).sub.3.
[0193] An EL device was prepared in the same manner as in Example 1
except for using the compound instead of Compound No. 1 and was
confirmed to emit red luminescence showing .lamda.max=G40 nm under
voltage application.
Example 11
##STR00059##
[0195] In a 200 ml-three-necked flask, 3.40 g (25.0 mmole) of
4-methylphenyl-boronic acid (made by Aldrich Co.), 4.09 g (25.0
mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of
ethanol and 25 mol of 2M-sodium carbonate aqueous solution were
placed and stirred at room temperature under nitrogen stream, and
0.98 g (0.85 mmole) of tetrakis(triphenylphosphine)-palladium (0)
was added thereto. Thereafter, reflux under stirring was perforated
for 8 hours under nitrogen stream. After completion of the
reaction, the reaction product was cooled and extracted by addition
of cold water and toluene. The organic layer was washed with saline
water and dried on magnesium sulfate, followed by removal of the
solvent under a reduced pressure to provide dry solid. The residue
was purified by silica gel column chromatography (eluent:
chloroform/methanol=10/1) to obtain 2.80 g (yield=51.1%) of
1-(4-methylphenyl)isoquinoline.
##STR00060##
[0196] In a 200 ml-three-necked flask, 0.58 mg (1.64 mmole) of
iridium (111) chloride-trihydrate (made by Acros Organics Co.),
1.61 g (7.34 mmole) of 1-(4-methylphenyl)isoquinoline, 45 ml of
ethanol and 15 ml of water were placed and stirred for 30 min. at
room temperature under nitrogen stream, followed by 24 hours of
reflux under stirring. The reaction product was cooled to room
temperature, and the precipitate was recovered by filtration and
washed with water, followed successive washing with ethanol and
acetone. After drying under a reduced pressure at room temperature,
1.02 g (yield=93.4%) of red powdery
tetrakis[1-(4-methylphenyl)isoquinoline-C.sup.2,N]-(.mu.-dichloro)diiridi-
um (III) (Example Compound No. 661) was obtained. FIG. 10 shows a
.sup.1H-NMR spectrum of a heavy chloroform solution of the
compound. A toluene solution of the compound exhibited a
luminescence spectrum showing .lamda.max=617 n and a quantum yield
of 0.46 relative to 1.0 of Ir(ppy).sub.3.
##STR00061##
[0197] In a 200 ml-three-necked flask, 70 ml of ethoxyethanol, 0.95
g (0.72 mmole) of
tetrakis[1-(4-methylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)-diiridi-
um (III), 0.22 g (2.10 mmole) of acetylacetone and 1.04 g (9.91
mmole) of sodium carbonate, were placed and stirred for 1 hour at
room temperature under nitrogen stream and then refluxed under
stirring for 15 hours. The reaction product was cooled with ice,
and the precipitate was filtered out and washed with water. The
precipitate was then purified by silica gel column chromatography
(eluent: chloroform/methanol=30/1) to obtain 0.43 g (yield=41.3%)
of red powdery
bis[1-(4-methylphenyl)isoquinoline-C.sup.2,N](acetylacetonato)-iridium
(III) (Example Compound No. 43). According to MALDI-TOF MS, M.sup.+
of 728.2 of the compound was confirmed. FIG. 11 shows a .sup.1H-NMR
of a heavy chloroform solution of the compound. A toluene solution
of the compound exhibited a luminescence spectrum showing
.lamda.max=622 nm and a quantum yield of 0.70 relative to 1.0 of
Ir(ppy).sub.3.
##STR00062##
[0198] In a 100 ml-three-necked flask, 0.27 g (1.27 mmole) of
1-(4-methylphenyl)isoquinoline, 0.36 g (0.49 mmole) of
bis[1-(4-methylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iridium
(Iii) and 25 ml of glycerol, were placed and heated around
180.degree. C. under stirring and nitrogen stream. The reaction
product was cooled to room temperature and poured info 170 ml of
1N-hydrochloric acid, and the precipitate was filtered out, washed
with water and dried at 100.degree. C. under a reduced pressure for
5 hours. The precipitate was purified by silica gel column
chromatography with chloroform as the eluent to obtain 0.27 g
(yield 64.5%) of red powdery
tris[1-(4-methylphenyl)-isoquinoline-C.sup.2,N]iridium (III)
(Example Compound No. 19). According to MALDI-TOF MS, M.sup.+ of
847.3 of the compound was confirmed. FIG. 12 shows a .sup.1H-NMR
spectrum of a heavy chloroform solution of the compound. A toluene
solution of the compound exhibited a luminescence spectrum showing
.lamda.max=619 nm and a quantum yield of 0.65 relative to 1.0 of
Ir(ppy).sub.3.
Example 12
[0199] The following compounds were successively produced in the
same manner as in Example 11 except for using
4-n-hexylphenylboronic acid instead of the 4-methylphenylboronic
acid.
[0200]
Tetrakis[1-(4-n-hexylphenyl)isoquinoline-C.sup.2,N[(.mu.-dichloro)d-
iiridium (Example Compound No. 667)
[0201] luminescence spectrum of toluene solution: .lamda.max=616
nm
[0202] quantum yield=0.40 relative to 1.0 of Ir(ppy).sub.3.
[0203]
Bis(1-(4-n-hexylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iri-
dium (III) (Example Compound No. 196)
[0204] MALDI-TOF MS: M.sup.+=868.4 luminescence spectrum of toluene
solution: .lamda.max=625 nm
[0205] quantum yield=0.87 relative to 1.0 of Ir(ppy).sub.3
[0206] Tris[1-(4-n-hexylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound. No. 192)
[0207] MALDI-TOF MS: M.sup.+=1057.5
[0208] luminescence spectrum of toluene solution: .lamda.max=621
nm
[0209] quantum yield=0.88 relative to 1.0 of Ir(ppy).sub.3
Example 13
[0210] The following compounds were successively produced in the
same manner as in Example 11 except for using
4-n-octylphenylboronic acid instead of the 4-methylphenylboronic
acid.
[0211]
Tetrakis[1-(4-n-octylphenyl)isoquinoline-C.sup.2,N[(.mu.-dichloro)d-
iiridium (Example Compound No. 669)
[0212] luminescence spectrum of toluene solution: .lamda.max=617
nm
[0213] quantum yield=0.47 relative to 1.0 of Ir(ppy).sub.3.
[0214]
Bis[1-(4-n-octylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iri-
dium (III) (Example Compound No. 218)
[0215] MALDI-TOF MS: M.sup.+=924.4
[0216] luminescence spectrum of toluene solution: .lamda.max=625
nm
[0217] quantum yield=1.05 relative to 1.0 of Ir(ppy).sub.3
[0218] FIG. 13 shows a .sup.1H-NMR spectrum of a heavy chloroform
solution of the compound.
[0219] Tris[1-(4-n-octylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 214)
[0220] MALDI-TOF MS: M.sup.+=1141.6.
[0221] luminescence spectrum of toluene solution: .lamda.max=620
nm
[0222] quantum yield=0.75 relative to 1.0 of Ir(ppy).sub.3
Example 14
[0223] The following compounds were successively produced in the
same manner as in Example 11 except for using
4-tart-butylphenylboronic acid (made by Aldrich Co.) instead of the
4-methylphenylboronic acid.
[0224]
Tetrakis[1-(4-t-butylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)d-
iiridium (Example Compound No. 665)
[0225] luminescence spectrum of toluene solution: .lamda.max=614
nm
[0226] quantum yield=0.39 relative to 1.0 of Ir(PPY).sub.3.
[0227]
Bis[1-(4-t-butylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iri-
dium (III) (Example Compound No. 174)
[0228] MALDI-TOF MS: M.sup.+=812.3
[0229] luminescence spectrum of toluene solution: .lamda.max=626
nm
[0230] quantum yield=0.66 relative to 1.0 of Ir(ppy).sub.3
[0231] Tris[1-(4-t-butylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 170)
[0232] MALDI-TOF MS: M.sup.+=973.4
[0233] luminescence spectrum of toluene solution: .lamda.max=618
nm
[0234] quantum yield=0.73 relative to 1.0 of Ir(ppy).sub.3
Example 15
[0235] The following compounds were successively produced in the
same manner as in Example 11 except for using 3-fluorophenylboronic
acid (made by Aldrich Co.) instead of the 4-methylphenylboronic
acid.
[0236]
Tetrakis[1-(5-fluorophenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)di-
iridium (Example Compound No. 684)
[0237] luminescence spectrum of toluene solution: .lamda.max=625
nm
[0238] quantum yield=0.22 relative to 1.0 of Ir(ppy).sub.3.
[0239]
Bis[1-(5-fluorophenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)irid-
ium (III) (Example Compound No. 47)
[0240] MALDI-TOF MS: M.sup.+=736.2
[0241] luminescence spectrum of toluene solution: .lamda.max=629
nm
[0242] quantum yield=0.65 relative to 1.0 of Ir(PPY).sub.3
[0243] Tris[1-(5-fluorophenyl)isoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 23)
[0244] MALDI-TOF MS: M.sup.+=859.2
[0245] luminescence spectrum of toluene solution: .lamda.max=626
nm
[0246] quantum yield=0.62 relative to 1.0 of Ir(ppy).sub.3
Example 16
[0247] The following compounds were successively produced in the
same manner as in Example 11 except for using
4-phenoxyphenylboronic acid instead of the 4-methylphenylboronic
acid.
[0248]
Bis[1-(4-phenoxyphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iri-
dium (III) (Example Compound No. 365)
[0249] MALDI-TOF MS: M.sup.+=884.2
[0250] luminescence spectrum of toluene solution: .lamda.max=608
nm
[0251] quantum yield=0.65 relative to 1.0 of Ir(ppy).sub.3
[0252] Tris[1-(4-phenoxyphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 361)
[0253] MALDI-TOF MS: M.sup.+=1081.3
[0254] luminescence spectrum of toluene solution: .lamda.max=604
nm
[0255] quantum yield=0.54 relative to 1.0 of Ir(PPY).sub.3
Example 17
[0256] The following compounds were successively produced in the
same manner as in Example 11 except for using 3-methylphenylboronic
acid instead of the 4-methylphenylboronic acid.
[0257]
Bis[1-(4-5-methylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)ir-
idium (III) (Example Compound No. 44)
[0258] MALDI-TOF MS: M.sup.+=728.2
[0259] luminescence spectrum of toluene solution: .lamda.max=638
nm
[0260] quantum yield=0.78 relative to 1.0 of Ir(ppy).sub.3
[0261] Tris[1-(4-5-methylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 20)
[0262] MALDI-TOF MS: M.sup.+=847.3
[0263] luminescence spectrum of toluene solution: .lamda.max=631
nm
[0264] quantum yield=0.71 relative to 1.0 of Ir(PPY).sub.3
Example 18
[0265] 1-phenylisoquinoline synthesized in Example 7 was used
instead of the 1-(4-methylphenyl)isoquinoline used in Example 11,
and the following compound was prepared in a similar manner as in
Example 11 via
tetrakis(1-phenylisoquinoline-C.sup.2,N)(.mu.-dichloro)-diiridium
(III) (Example Compound No. 660).
[0266] Bis(1-phenylisoquinoline-C.sup.2,N)(acetylacetonato)-iridium
(III) (Example Compound No. 42)
[0267] MALDI-TOF MS: M.sup.+=700.2
[0268] luminescence spectrum of toluene solution: .lamda.max=604
am
[0269] quantum yield=0.54 relative to 1.0 of Ir(PPY).sub.3
Example 19
[0270] 1-(biphenyl-3-yl)isoquinoline was synthesized by using
3-biphenylboronic acid (made by Frontier Scientific, Inc.) instead
of phenylboronic acid in Example 7, and similarly as in Example 7,
tris[1-(biphenyl-3-yl)isoquinoline-C.sup.2,N]iridium (III) (Example
Compound No. 3) was prepared from the 1-(biphenyl-3-yl)isoquinoline
and iridium (III) acetylacetonate. According to MALDI-TOF MS,
M.sup.+ of the compound of 1033.3 was confirmed. A toluene solution
of the compound exhibited a luminescence spectrum showing
.lamda.max=621 nm and a quantum yield of 0.53 relative to 1.0 of
Ir(ppy).sub.3.
Example 20
[0271] 3-methyl-2,4-pentanedione (made by Aldrich Co.) instead of
acetylacetone in Example 11, and similarly as in Example 11,
bis[1-(4-methylphenyl)-isoquinoline-C.sup.2,N](3-methyl-2,4-pentanedionat-
o)-iridium (III) (Example Compound No. 126) was synthesized.
According to MALDI-TOF MS, M.sup.+ of the compound of 742.2 was
confirmed. A toluene solution of the compound exhibited a
luminescence spectrum showing .lamda.max=627 nm and a quantum yield
of 0.81 relative to 1.0 of Ir(ppy).sub.3.
Example 21
[0272] 2,2,6,6-tetramethyl-3,5-heptanedione (made by Tokyo Kasei
Kogyo) was used instead of acetylacetone in Example 11, and
similarly as in Example 11,
bis[1-(4-methylphenyl)isoquinoline-C.sup.2,N](2,2,6,6-tetramethyl-3,5-hep-
tanedionato)iridium (III) (Example Compound No. 127) was
synthesized. According to MALDI-TOF MS, M.sup.+ of the compound of
812.3 was confirmed. A toluene solution of the compound exhibited a
luminescence spectrum showing .lamda.max=624 nm and a quantum yield
of 0.76 relative to 1.0 of Ir(PPY).sub.3.
Example 22
[0273] 2-Phenylpyridine was used instead of the
1-(4-methylphenyl)isoquinoline used in Example 11, and similarly as
in Example 11,
bis(2-phenylpyridine-C.sup.2,N)(acetylacetonato)iridium (III) was
synthesized via
(2-phenylpyridine-C.sup.2,N)(.mu.-dichloro)diiridium (III). The
compound was reacted with 1-phenylisoquinoline synthesized in
Example 7 in a similar manner as in Example 11 to obtain
bis(2-phenylpyridine-C.sup.2,N)(1-phenylisoquinoline-C.sup.2,N)iridium
(III) (Example Compound No. 64). According to MALDI-TOF MS, M.sup.+
of the compound of 705.2 was confirmed. A toluene solution of the
compound exhibited a luminescence spectrum showing .lamda.max=618
nm and a quantum yield of 0.43 relative to 1.0 of
Ir(ppy).sub.3.
Example 23
[0274] Bis(1-phenylisoquinoline-C.sup.2,N)(acetyl-acetonato)iridium
(III) synthesized in Example 18 and 2-phenylpyridine were reacted
in a similar manner as in Example 22 to obtain
bis(1-phenylisoquinoline-C.sup.2,N)(2-phenylpyridine-C.sup.2,N)iridium
(III) (Example Compound No. 31). According to MALDI-TOF MS, M.sup.+
of the compound of 755.2 was confirmed. A toluene solution of the
compound exhibited a luminescence spectrum showing .lamda.max=617
nm and a quantum yield of 0.46 relative to 1.0 of
Ir(ppy).sub.3.
Example 24
[0275] The following compounds were successively produced in the
same manner as in Example 11 except for using 4-butylphenylboronic
acid (made by Lancaster Synthesis Co.) instead of the
4-methylphenylboronic acid.
[0276]
Tetrakis[1-(4-n-butylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)d-
iiridium (Example Compound No. 664)
[0277] luminescence spectrum of toluene solution: .lamda.max=629
nm
[0278] quantum yield=0.44 relative to 1.0 of Ir(ppy).sub.3.
[0279]
Bis[1-(4-butylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iridi-
um (III) (Example Compound No. 163)
[0280] MALDI-TOF MS: M.sup.+=812.0
[0281] luminescence spectrum of toluene solution: .lamda.max=626
nm
[0282] quantum yield=0.81 relative to 1.0 of Ir(ppy).sub.3
[0283] Tris[1-(4-butylphenyl)isoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 159)
[0284] MALDI-TOF MS: M.sup.+=973.3
[0285] luminescence spectrum of toluene solution: .lamda.max=621
nm
[0286] quantum yield=0.82 relative to 1.0 of Ir(PPY).sub.3.
Example 25
[0287] 5-Aminoisoquinoline (made by Tokyo Kasei Kogyo K.K.) was
used to synthesize 1-chloro-5-fluoroisoquinoline along the
following path with yields as indicated.
##STR00063##
[0288] In the process of Example 11, phenylboronic acid was used
instead of the 4-methylphenyl-boronic acid and
1-chloro-5-fluoroisoquinoline was used instead of the
1-chloroisoquinoline to synthesize 1-phenyl-5-fluoroisoquinoline,
which was used instead of the 1-(4-methylphenyl)isoquinoline
otherwise in a similar manner as in Example 11 to synthesize the
following compounds successively.
[0289]
Tetrakis(1-phenyl-5-fluoroisoquinoline-C.sup.2,N)(.mu.-dichloro)dii-
ridium (III) (Example Compound No. 704)
[0290] luminescence spectrum of toluene solution: .lamda.max=620
nm
[0291] quantum yield=0.38 relative to 1.0 of Ir(PPY).sub.3.
[0292]
Bis(1-phenyl-5-fluoroisoquinoline-C.sup.2,N)-(acetylacetonato)iridi-
um (III) (Example Compound No. 240)
[0293] MALDI-TOF MS: M.sup.+=735.8
[0294] luminescence spectrum of toluene solution: .lamda.max=636
nm
[0295] quantum yield=0.70 relative to 1.0 of Ir(ppy).sub.3
[0296] Tris(1-phenyl-5-fluoroisoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 155)
[0297] MALDI-TOF MS: M.sup.+=858.9
[0298] luminescence spectrum of toluene solution: .lamda.max=628
nm
[0299] quantum yield=0.55 relative to 1.0 of Ir(PPY).sub.3
Example 26
[0300] 3-Nitro-2-hydroxypyridine (made by Aldrich Co.) was used to
synthesize 1-chloro-8-azaisoquinoline along the following path.
"Sulfo mix" used for the ring closure was prepared through a
process described in J. Org. Chem., 1943, 8, 544-549.
##STR00064##
[0301] The above-obtained 1-chloro-8-azaisoquinoline was used
instead of the 1-chloroisoquinoline in Example 7 to synthesize
1-phenyl-8-azaisoquinoline, which was used instead of the
1-(4-methylphenyl)-isoquinoline otherwise in the same manner as in
Example 11 to prepare the following compounds successively.
[0302]
Tetrakis(1-phenyl-8-azaphenylisoquinoline-C.sup.2,N)(.mu.-dichloro)-
diiridium (III) (Example Compound No. 755)
[0303] luminescence spectrum of toluene solution: .lamda.max=635
nm
[0304] quantum yield=0.40 relative to 1.0 of Ir(PPY).sub.3.
[0305]
Bis(1-phenyl-8-azaphenylisoquinoline-C.sup.2,N)-(acetylacetonato)ir-
idium (III) (Example Compound No. 612)
[0306] MALDI-TOF MS: M.sup.+=701.1
[0307] luminescence spectrum of toluene solution: .lamda.max=631
nm
[0308] Tris(1-phenyl-8-azaphenylisoquinoline-C.sup.2,N)-iridium
(III) (Example Compound No. 609) MALDI-TOF MS: M.sup.+=807.9
[0309] luminescence spectrum of toluene Solution: .lamda.max=622
nm
Example 27
[0310] An EL device having a laminate structure as shown in FIG.
1(b) was prepared. On an ITO electrode 14 patterned on a 1.1
mm-thick alkali-free glass substrate 15, .alpha.-NPD was deposited
in a thickness of 40 nm at a vacuum deposition rate of 0.1 nm/sec
at a vacuum pressure of 10.sup.-4 Pa to form a hole-transporting
layer 13, and then CBP and
tris(1-phenylisoquinoline-C.sup.2,N)iridium (III) (Example.
Compound No. 1) in an amount of providing a concentration of 9%
were co-vacuum-deposited to form a 40 nm-thick luminescence layer
12 while controlling the heating conditions of the vacuum
deposition boats so as to provide vacuum deposition rates of 0.1
nm/sec for CBP and 0.09 nm/sec for the iridium complex.
[0311] Then, an electron-transporting layer was formed in a
thickness of 40 nm by vacuum deposition of bathophenanthroline
Bphen represented by a structural formula shown below at a rate of
0.1 nm/sec.
##STR00065##
[0312] Thereon, a ca. 1 nm-thick potassium fluoride layer was
formed as an electron-transporting layer 16 by vacuum deposition at
a rate of 0.5 nm/sec, and then aluminum was vacuum-deposited in a
thickness of 150 nm at a rate of 1 nm/sec to provide a cathode
metal 11.
[0313] The device of this Example was prepared while aiming at the
effects of (1) increased supply of electrons and suppression of
hole leakage by use of Bphen, (2) improved electron-injection
characteristic by use of KF and (3) optimization of optical layer
thickness. The voltage-efficiency-luminance characteristics of the
thus-obtained device are shown in FIG. 5.
[0314] The device of this Example succeeded in realizing
efficiencies of 6.2 lm/W and 5.2 lm/W at luminances of 100
cd/m.sup.2 and 300 cd/m.sup.2, respectively. CIE coordinates were
(0.68, 0.317) at 40 cd/m.sup.2, (0.682, 0.315) at 113 cd/m.sup.2
and (0.678, 0.317) at 980 cd/m.sup.2, thus showing that a
sufficient color purity was provided according to a color standard
of the NTSC. Thus, the luminescence color was substantially
unchanged at different luminances and voltages.
[0315] Tris(1-phenylisoquinoline-C.sup.2,N)iridium (III) having a
ligand of 1-phenylisoquinoline can provide red luminescence
according to the NTSC standard even without adding a substituent to
the ligand skeleton for luminescence color adjustment of the
complex, and is thus excellent as a red luminescence material.
Further, it is also a desirable luminescence material from a
practical viewpoint of shorter synthesis steps as the effect is
attained by using a ligand having no substituent.
[0316] The drive conditions included an application voltage V=5
volts and a current J=1.5 mA/cm.sup.2 at a luminance of 300
cd/m.sup.2, and also 10 volts and 520 mA/cm.sup.2 at 14000
cd/m.sup.2. The external quantum efficiency (E.Q.E.) values (%) of
the thus-prepared EL device are plotted on FIG. 6 and showing
efficiencies remarkably improving the efficiency of the
conventional EL device, e.g., over 10% at 100 cd/m.sup.2.
Example 28
[0317] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-ethylphenylboronic acid (made by Lancaster Co.) instead of the
4-methylphenylboronic acid in Example 11.
[0318]
Tetrakis[1-(4-ethylphenyl)isoquinoline-C.sup.2,N(.mu.-dichloro)irid-
ium (III) (Example Compound No. 662),
[0319]
Bis[1-(4-ethylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iridi-
um (III) (Example Compound No. 137),
[0320] Tris[1-(4-ethylphenyl)isoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 135).
Example 29
[0321] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-propylphenylboronic acid instead of the 4-methylphenylboronic
acid in Example 11.
[0322]
Tetrakis[1-(4-propylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)ir-
idium (III) (Example Compound No. 663);
[0323]
Bis[1-(4-propylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)irid-
ium (III) (Example Compound No. 148),
[0324] Tris[1-(4-propylphenyl)isoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 144).
Example 30
[0325] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-isopropylphenylboronic acid (made by Lancaster Co.) instead of
the 4-methylphenylboronic acid in Example 11.
[0326]
Tetrakis[1-(4-isopropylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro-
)iridium (III),
[0327]
Bis[1-(4-isopropylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)i-
ridium (III),
[0328] Tris[1-(4-isopropylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 146).
Example 31
[0329] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-n-pentylphenylboronic acid instead of the 4-methylphenylboronic
acid in Example 11.
[0330]
Tetrakis[1-(4-n-pentylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)-
iridium (III) (Example Compound No. 666),
[0331]
Bis[1-(4-n-pentylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)ir-
idium (III) (Example Compound No. 185),
[0332] Tris[1-(4-n-pentylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 181).
Example 32
[0333] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-n-heptylphenylboronic acid instead of the 4-methylphenylboronic
acid in Example 11.
[0334]
Tetrakis[1-(4-n-heptylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)-
iridium (III) (Example Compound No. 660),
[0335]
Bis[1-(4-n-heptylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)ir-
idium (III) (Example Compound No. 207),
[0336] Tris[1-(4-n-heptylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 203).
Example 33
[0337] The following compounds were successively produced in the
same manner as in Example 11 except for using 4-fluorophenylboronic
acid (made by Aldrich Co.) instead of the
4-methylphenylboronic'acid.
[0338]
Tetrakis[1-(4-n-hexylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)d-
iiridium (Example Compound No. 683)
[0339] luminescence spectrum of toluene solution: .lamda.max=602
nm
[0340] quantum yield=0.40 relative to 1.0 of Ir(ppy).sub.3.
[0341]
Bis[1-(4-fluorohexylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato-
)iridium (III) (Example Compound No. 46)
[0342] MALDI-TOF MS: M.sup.+=737.2
[0343] luminescence spectrum of toluene solution: .lamda.max=603
nm
[0344] quantum yield=0.95 relative to 1.0 of Ir(ppy).sub.3
[0345] Tris[1-(4-fluorophenyl)isoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 22)
[0346] MALDI-TOF MS: M.sup.+=859.2
[0347] luminescence spectrum of toluene solution: .lamda.max=596
nm
[0348] quantum yield=0.92 relative to 1.0 of Ir(ppy).sub.3
Example 34
[0349] The following compounds were successively produced in the
same manner as in Example 11 except for using
4-fluoro-3-methylphenylboronic acid (made by Aldrich Co.) instead
of the 4-methylphenylboronic acid.
[0350]
Tetrakis[1-(4-fluoro-5-methylphenyl)isoquinoline-C.sup.2,N](.mu.-di-
chloro)diiridium (Example Compound No. 738)
[0351] luminescence spectrum of toluene solution: .lamda.max=618
nm
[0352]
Bis[1-(4-fluoro-5-methylphenyl)isoquinoline-C.sup.2,N]-(acetylaceto-
nato)iridium (III) (Example Compound No. 222)
[0353] MALDI-TOF MS: M.sup.+=765.2
[0354] luminescence spectrum of toluene solution: .lamda.max=615
nm
[0355]
Tris[1-(4-fluoro-5-methylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 226)
[0356] MALDI-TOF MS: M.sup.+=901.1
[0357] luminescence spectrum of toluene solution: .lamda.max=616
nm
Example 35
[0358] The following compounds were successively produced in the
same manner as in Example 11 except for using
4-trifluoromethylphenylboronic acid (made by Lancaster Co.) instead
of the 4-methylphenylboronic acid.
[0359]
Tetrakis[1-(4-trifluoromethylphenyl)isoquinoline-C.sup.2,N[(.mu.-di-
chloro)diiridium
[0360] luminescence spectrum of toluene solution: .lamda.max=614
nm
[0361]
Bis[1-(4-trifluoromethylphenyl)isoquinoline-C.sup.2,N]-(acetylaceto-
nato)iridium (III)
[0362] MALDI-TOF MS: M.sup.+=836.1
[0363] luminescence spectrum of toluene solution: .lamda.max=623
nm
[0364] quantum yield=0.23 relative to 1.0 of Ir(PPY).sub.3
[0365]
Tris[1-(4-trifluoromethylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 11)
[0366] MALDI-TOF MS: M.sup.+=1009.2
[0367] luminescence spectrum of toluene solution: .lamda.max=608
nm
[0368] quantum yield=0.48 relative to 1.0 of Ir(ppy).sub.3.
Example 36
[0369] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3-trifluoromethylphenylboronic acid (made by. Lancaster Co.)
instead of the 4-methylphenylboronic acid in Example 11.
[0370]
Tetrakis[1-(5-trifluoromethylphenyl)isoquinoline-C.sup.2,N](.mu.-di-
chloro)iridium (III)
[0371]
Bis[1-(5-trifluoromethylphenyl)isoquinoline-C.sup.2,N]-(acetylaceto-
nato)iridium (III)
[0372]
Tris[1-(5-trifluoromethylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 12).
Example 37
[0373] The following compounds were successively produced in the
same manner as in Example 11 except for using
3,5-difluoro-3-methylphenylboronic acid (made by Aldrich Co.)
instead of the 4-methylphenylboronic acid.
[0374]
Tetrakis[1-(3,5-difluoro-3-methylphenyl)isoquinoline-C.sup.2,N](.mu-
.-dichloro)diiridium (Example Compound No. 686)
[0375] luminescence spectrum of toluene solution: .lamda.max=618
nm
[0376]
Bis[1-(3,5-fluoro-3-methylphenyl)isoquinoline-C.sup.2,N]-(acetylace-
tonato)iridium (III) (Example Compound No. 425)
[0377] MALDI-TOF MS: M.sup.+=765.2
[0378] luminescence spectrum of toluene solution: .lamda.max=625
nm
[0379]
Tris[1-(3,5-difluoro-3-methylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 421)
[0380] MALDI-TOF MS: M.sup.+=901.2
[0381] luminescence spectrum of toluene solution: .lamda.max=616
nm
Example 38
[0382] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
2,3-difluorophenylboronic acid instead of the 4-methylphenylboronic
acid in Example 11.
[0383]
Tetrakis[1-(5,6-difluorophenyl)isoquinoline-C.sup.2,N](.mu.-dichlor-
o)iridium (III)
[0384]
Bis[1-(5,6-difluorophenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)-
iridium (III) (Example Compound No. 501),
[0385] Tris[1-(5,6-difluorophenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 497).
Example 39
[0386] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
2,3-difluoro-4-n-butylphenylboronic acid instead of the
4-methylphenylboronic acid in Example 11.
[0387]
Tetrakis[1-(4-n-butyl-5,6-difluorophenyl)-isoquinoline-C.sup.2,N](.-
mu.-dichloro)iridium (III) (Example Compound No. 698),
[0388]
Bis[1-(4-n-butyl-5,6-difluorophenyl)isoquinoline-C.sup.2,N]-(acetyl-
acetonato)iridium(III) (Example Compound No. 534),
[0389]
Tris[1-(4-n-butyl-5,6-difluorophenyl)isoquinoline-C.sup.2,N]-iridiu-
m (III) (Example Compound No. 530).
Example 40
[0390] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
1-phenyl-5-trifluoromethylisoquinoline, synthesized in the same
manner as in Example 7 by using
1-chloro-5-trifluoromethylisoquinoline instead of the
1-chloroisoquinoline in Example 7.
[0391]
Tetrakis[1-phenyl-5-trifluoromethylisoquinoline-C.sup.2,N](.mu.-dic-
hloro)iridium (III) (Example Compound No. 706).
[0392]
Bis[1-phenyl-5-trifluoromethylisoquinoline-C.sup.2,N]-(acetylaceton-
ato)iridium (III),
[0393]
Tris[1-phenyl-5-trifluoromethylisoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 83).
Example 41
[0394] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
1-phenyl-4-trifluoromethylisoquinoline, synthesized in the same
manner as in Example 7 by using
1-chloro-4-trifluoromethylisoquinoline instead of the
1-chloroisoquinoline in Example 7.
[0395]
Tetrakis[1-phenyl-4-trifluoromethylisoquinoline-C.sup.2,N](.mu.-dic-
hloro)iridium (III) (Example Compound No. 706),
[0396]
Bis[1-phenyl-4-trifluoromethylisoquinoline-C.sup.2,N]-(acetylaceton-
ato)iridium (III),
[0397]
Tris(1-phenyl-4-trifluoromethylisoquinoline-C.sup.2,N)-iridium
(III) (Example Compound No. 82).
Example 42
[0398] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
1-phenyl-4-trifluoromethylisoquinoline, synthesized in the same
manner as in Example 7 by using
1-chloro-4-trifluoromethylisoquinoline instead of the
1-chloroisoquinoline in Example 7.
[0399]
Tetrakis[1-phenyl-4-trifluoroisoquinoline-C.sup.2,N](.mu.-dichloro)-
iridium (III) (Example Compound No. 705).
[0400]
Bis[1-phenyl-4-trifluoroisoquinoline-C.sup.2,N]-(acetylacetonato)ir-
idium (III),
[0401] Tris[1-phenyl-4-trifluoroisoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 81).
Example 43
[0402] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3,5-difluorophenylboronic acid and 1-chloro-5-fluoroisoquinoline
instead of the 4-methylphenylboronic acid and 1-chloroisoquinoline,
respectively, in Example 11.
[0403]
Tetrakis[1-(3,5-difluorophenyl)-5-fluoroisoquinoline-C.sup.2,N](.mu-
.-dichloro)diiridium (III).
[0404]
Bis[1-(3,5-difluorophenyl)-5-fluoroisoquinoline-C.sup.2,N](acetylac-
etonato)iridium (III).
[0405]
Tris[1-(3,5-difluorophenyl)-5-fluoroisoquinoline-C.sup.2,N]iridium
(III) (Example Compound No. 232).
Example 44
[0406] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-difluorophenylboronic acid and 1-chloro-4-fluoroisoquinoline
instead of the 4-methylphenylboronic acid and 1-chloroisoquinoline,
respectively, in Example 11.
[0407]
Tetrakis[1-(4-difluorophenyl)-4-fluoroisoquinoline-C.sup.2,N](.mu.--
dichloro)diiridium (III):
[0408]
Bis[1-(4-difluorophenyl)-4-fluoroisoquinoline-C.sup.2,N](acetylacet-
onato)iridium (III).
[0409]
Tris[1-(4-difluorophenyl)-4=fluoroisoquinoline-C.sup.2,N]iridium
(III) (Example Compound No. 230).
Example 45
[0410] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-difluorophenylboronic acid and 1-chloro-5-fluoroisoquinoline
instead of the 4-methylphenylboronic acid and 1-chloroisoquinoline,
respectively, in Example 11.
[0411]
Tetrakis[1-(4-difluorophenyl)-5-fluoroisoquinoline-C.sup.2,N](.mu.--
dichloro)diiridium (III).
[0412]
Bis[1-(4-difluorophenyl)-5-fluoroisoquinoline-C.sup.2,N](acetylacet-
onato)iridium (III).
[0413]
Tris[1-(4-difluorophenyl)-5-fluoroisoquinoline-C.sup.2,N]iridium
(III) (Example Compound No. 228).
Example 46
[0414] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-trifluoromethylphenylboronic acid and
1-chloro-4-fluoroisoquinoline instead of the 4-methylphenylboronic
acid and 1-chloroisoquinoline, respectively, in Example 11.
[0415]
Tetrakis[1-(4-trifluorofluorophenyl)-4-fluoroisoquinoline-C.sup.2,N-
](.mu.-dichloro)diiridium (III).
[0416]
Bis[1-(4-trifluoromethylphenyl)-4-fluoroisoquinoline-C.sup.2,N](ace-
tylacetonato)iridium (III).
[0417]
Tris[1-(4-trifluoromethylphenyl)-4-fluoroisoquinoline-C.sup.2,N]iri-
dium (III) (Example Compound No. 256).
Example 47
[0418] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-fluorophenylboronic acid and
1-chloro-4-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0419]
Tetrakis[1-(4-fluorophenyl)-4-trifluoromethylquinoline-C.sup.2,N](.-
mu.-dichloro)diiridium (III).
[0420]
Bis[1-(4-fluorophenyl)-4-trifluoromethylquinoline-C.sup.2,N](acetyl-
acetonato)iridium (III).
[0421]
Tris[1-(4-fluorophenyl)-4-trifluoromethylisoquinoline-C.sup.2,N]iri-
dium (III) (Example Compound No. 231).
Example 48
[0422] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-fluorophenylboronic acid and 1-chloro-5-fluoroisoquinoline
instead of the 4-methylphenylboronic acid and 1-chloroisoquinoline,
respectively, in Example 11.
[0423]
Tetrakis[1-(4-fluorophenyl)-5-trifluoromethylisoquinoline-C.sup.2,N-
](.mu.-dichloro)diiridium (III).
[0424]
Bis[1-(4-fluorophenyl)-5-trifluoromethylisoquinoline-C.sup.2,N](ace-
tylacetonato)iridium (III).
[0425]
Tris[1-(4-fluorophenyl)-5-trifluoromethylisoquinoline-C.sup.2,N]iri-
dium (III) (Example Compound No. 229).
Example 49
[0426] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-trifluoromethylphenylboronic acid and
1-chloro-4-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0427]
Tetrakis[1-(4-trifluoromethylphenyl)-4-trifluoromethylisoquinoline--
C.sup.2,N](.mu.-dichloro)diiridium (III) (Example Compound No.
691).
[0428]
Bis[1-(4-trifluoromethylphenyl)-4-trifluoromethylisoquinoline-C.sup-
.2,N](acetylacetonato)iridium (III).
[0429]
Tris[1-(4-trifluoromethylphenyl)-4-trifluoromethylisoquinoline-C.su-
p.2,N]iridium (III) (Example Compound No. 260).
Example 50
[0430] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-trifluoromethylphenylboronic acid and
1-chloro-5-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0431]
Tetrakis[1-(4-trifluoromethylphenyl)-5-trifluoromethylisoquinoline--
C.sup.2,N](.mu.-dichloro)diiridium (III).
[0432]
Bis[1-(4-trifluoromethylphenyl)-5-trifluoromethylisoquinoline-C.sup-
.2,N](acetylacetonato)iridium (III).
[0433]
Tris[1-(4-trifluoromethylphenyl)-5-trifluoromethylisoquinoline-C.su-
p.2,N]iridium (III) (Example Compound No. 255).
Example 51
[0434] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3,4,5-trifluorophenylboronic acid (made by Lancaster Co.) and
1-chloro-4-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0435]
Tetrakis[1-(3,4,5-trifluorophenyl)-4-trifluoromethylquinoline-C.sup-
.2,N](.mu.-dichloro)diiridium (III).
[0436]
Bis[1-(3,4,5-trifluorophenyl)-4-trifluoromethylisoquinoline-C.sup.2-
,N](acetylacetonato)iridium (III).
[0437]
Tris[1-(3,4,5-trifluorophenyl)-4-trifluoromethylisoquinoline-C.sup.-
2,N]iridium (III) (Example Compound No. 253).
Example 52
[0438] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3,4,5-trifluorophenylboronic acid (made by Lancaster Co.) and
1-chloro-5-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0439]
Tetrakis[1-(3,4,5-trifluorophenyl)-5-trifluoromethylisoquinoline-C.-
sup.2,N](.mu.-dichloro)diiridium (III).
[0440]
Bis[1-(3,4,5-trifluorophenyl)-5-trifluoromethylisoquinoline-C.sup.2-
,N](acetylacetonato)iridium (III).
[0441]
Tris[1-(3,4,5-trifluorophenyl)-5-trifluoromethylisoquinoline-C.sup.-
2,N]iridium (III) (Example Compound No. 250).
Example 53
[0442] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3,4,5,6-tetrafluorophenylboronic acid and
1-chloro-4-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0443]
Tetrakis[1-(3,4,5,6-tetrafluorophenyl)-4-trifluoromethylisoquinolin-
e-C.sup.2,N](.mu.-dichloro)diiridium (III).
[0444]
Bis[1-(3,4,5,6-trifluorophenyl)-4-trifluoromethylisoquinoline-C.sup-
.2,N](acetylacetonato)iridium (III).
[0445]
Tris[1-(3,4,5,6-tetrafluorophenyl)-4-trifluoromethylisoquinoline-C.-
sup.2,N]iridium (III) (Example Compound No. 268).
Example 54
[0446] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3,4,5,6-tetrafluorophenylboronic acid and
1-chloro-5-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0447]
Tetrakis[1-(3,4,5,6-tetrafluorophenyl)-5-trifluoromethylisoquinolin-
e-C.sup.2,N](.mu.-dichloro)diiridium (III) (Example Compound No.
690).
[0448]
Bis[1-(3,4,5,6-tetrafluorophenyl)-5-trifluoromethylisoquinoline-C.s-
up.2,N](acetylacetonato)iridium (III).
[0449]
Tris[1-(3,4,5,6-tetrafluorophenyl)-5-trifluoromethylisoquinoline-C.-
sup.2,N]iridium (III) (Example Compound No. 272).
Example 55
[0450] It is easy to synthesize
1-chloro-3,4,5,6,7,8-hexafluoroisoquinoline along the following
path according to processes described in references: J. Chem. Soc.
C, 1966, 2328-2331; J. Chem. Soc. C, 1971, 61-67; J. Org. Chem.,
1971, 29, 329-332 and Org, Syn., 1960, 40, 7-10:
##STR00066##
[0451] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3,4,5,6-tetrafluorophenylboronic acid and the above-synthesized
1-chloro-3,4,5,6,7,8-hexafluoroisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0452]
Tetrakis[1-(3,4,5,6-tetrafluorophenyl)-3,4,5,6,7,8-hexafluoroisoqui-
noline-C.sup.2,N](.mu.-dichloro)diiridium (III) (Example Compound
No. 709).
[0453]
Bis[1-(3,4,5,6-tetrafluorophenyl)-3,4,5,6,7,8-hexafluoroisoquinolin-
e-C.sup.2,N](acetylacetonato)iridium (III) (Example Compound No.
457).
[0454]
Tris[1-(3,4,5,6-tetrafluorophenyl)-3,4,5,6,7,8-hexafluoroisoquinoli-
ne-C.sup.2,N]iridium (III) (Example Compound No. 454).
Example 56
[0455] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3-isopropylphenylboronic acid (made by Lancaster Co.) instead of
the 4-methylphenylboronic acid in Example 11.
[0456]
Tetrakis[1-(5-isopropylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro-
)iridium (III),
[0457]
Bis[1-(5-isopropylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)i-
ridium (III),
[0458] Tris[1-(5-isopropylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 315).
Example 57
[0459] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3-butylphenylboronic acid instead of the 4-methylphenylboronic acid
in Example 11.
[0460]
Tetrakis[1-(5-butylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)iri-
dium (III) (Example Compound No. 725),
[0461]
Bis[1-(5-butylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iridi-
um (III),
[0462] Tris[1-(5-butylphenyl)isoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 316).
Example 58
[0463] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3-octylphenylboronic acid (made by Lancaster Co.) instead of the
4-methylphenylboronic acid in Example 11.
[0464]
Tetrakis[1-(5-octylphenyl)isoquinoline-C.sup.2N(.mu.-dichloro)iridi-
um (III) (Example Compound No. 730),
[0465]
Bis[1-(5-octylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iridi-
um (III),
[0466] Tris[1-(5-octylphenyl)isoquinoline-C.sup.2,N]-iridium (III)
(Example Compound No. 321).
Example 59
[0467] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3-methoxyphenylboronic acid (made by Lancaster Co.) instead of the
4-methylphenylboronic acid in Example 11.
[0468]
Tetrakis[1-(5-methoxyphenyl)isoquinoline-C.sup.2,N(.mu.-dichloro)ir-
idium (III),
[0469]
Bis[1-(5-methoxyphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)iri-
dium (III),
[0470] Tris[1-(5-methoxyphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 375).
Example 61
[0471] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-trifluoromethoxyphenylboronic acid (made by Aldrich Co.) and
1-chloro-4-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0472]
Tetrakis[1-(4-trifluoromethoxyphenyl)-4-trifluoromethylisoquinoline-
-C.sup.2,N](.mu.-dichloro)diiridium (III).
[0473]
Bis[1-(4-trifluoromethoxyphenyl)-4-trifluoromethylisoquinoline-C.su-
p.2,N](acetylacetonato)iridium (III).
[0474]
Tris[1-(trifluoromethoxyphenyl)-4-trifluoromethylisoquinoline-C.sup-
.2,N]iridium (III) (Example Compound No. 411).
Example 62
[0475] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-trifluoromethoxyphenylboronic acid and
1-chloro-5-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0476]
Tetrakis[1-(4-trifluoromethoxyphenyl)-5-trifluoromethylisoquinoline-
-C.sup.2,N](.mu.-dichloro)diiridium (111).
[0477]
Bis[1-(4-trifluoromethoxyphenyl)-5-trifluoromethylisoquinoline-C.su-
p.2,N](acetylacetonato)iridium (III).
[0478]
Tris[1-(4-trifluoromethoxyphenyl)-5-trifluoromethylisoquinoline-C.s-
up.2,N]iridium (III) (Example Compound No. 410).
Example 63
[0479] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-trifluoromethoxyphenylboronic acid and
1-chloro-4-fluoroisoquinoline instead of the 4-methylphenylboronic
acid and 1-chloroisoquinoline, respectively, in Example 11.
[0480]
Tetrakis[1-(4-trifluoromethoxyphenyl)-4-fluoroisoquinoline-C.sup.2,-
N](.mu.-dichloro)diiridium (III).
[0481]
Bis[1-(4-trifluoromethoxyphenyl)-4-fluoroisoquinoline-C.sup.2,N](ac-
etylacetonato)iridium (III).
[0482]
Tris[1-(4-trifluoromethoxyphenyl)-4-fluoroisoquinoline-C.sup.2,N]ir-
idium (III) (Example Compound No. 409).
Example 64
[0483]
Bis[1-(4-propylphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)irid-
ium (III) is synthesized in a similar manner as in Example 11 by
using 1-(4-propylphenyl)isoquinoline of Example 29 and via
tetrakis[1-(4-propylphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro)diiridiu-
m (III). It is easy to synthesize
bis[1-(4-propylphenyl)isoquinoline-C.sup.2,N](1-phenylisoquinoline-C.sup.-
2,N)iridium (III) (Example Compound No. 283) by reacting the
compound with 1-phenylisoquinoline of Example 7.
Example 65
[0484] Bis[1-phenylisoquinoline-C.sup.2,N]-(acetylacetonato)iridium
(III) is synthesized in a similar manner as in Example 11 by using
1-phenylisoquinoline instead of 1-(4-methylphenyl)isoquinoline of
Example 11 and via
tetrakis[1-phenylisoquinoline-C.sup.2,N](.mu.-dichloro)diiridium
(III). It is easy to synthesize
bis(1-isoquinoline-C.sup.2,N)[1-(4-propylphenyl)-isoquinoline-C.sup.2,N)i-
ridium (III) (Example Compound No. 299) by reacting the compound
with 1-(4-propylphenyl)-isoquinoline of Example 29.
Example 66
[0485] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using
1-(4-hexylphenyl)isoquinoline instead of the 2-phenylpyridine used
in Example 22.
[0486]
Bis[1-(4-hexylphenyl)isoquinoline-C.sup.2,N](1-phenylisoquinoline-C-
.sup.2,N)iridium (III) (Example Compound No. 287).
Example 67
[0487] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using 1-phenylisoquinoline and
1-(4-hexylphenyl)-isoquinoline instead of the 2-phenylpyridine and
1-phenylisoquinoline, respectively, in Example 22.
[0488]
Bis(1-phenylisoquinoline-C.sup.2,N)[1-(4-hexyphenyl)isoquinoline-C.-
sup.2,N]iridium (III) (Example Compound No. 303).
Example 68
[0489] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using
1-(4-octylphenyl)isoquinoline instead of the 2-phenylpyridine in
Example 22.
[0490]
Bis[1-(4-octylphenyl)isoquinoline-C.sup.2,N](1-phenylisoquinoline-C-
.sup.2,N)iridium (III) (Example Compound No. 289).
Example 69
[0491] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using 1-phenylisoquinoline and
1-(4-octylphenyl)-isoquinoline instead of the 2-phenylpyridine and
1-phenylisoquinoline, respectively, in Example 22.
[0492]
Bis(1-phenylisoquinoline-C.sup.2,N)[1-(4-octylphenyl)isoquinoline-C-
.sup.2,N]iridium (III) (Example Compound No. 305).
Example 70
Preparation of Activated Copper Powder
[0493] 400 g (2.5 mmole) of copper sulfate is dissolved in 2500 ml
of hot water and then cooled, and 219 mg (3.35 mole) of zinc powder
is added thereto at the same temperature. After washing with water
by decantation, 5%-hydrochloric acid is added thereto until
hydrogen gas generation is terminated to dissolve the zinc. Copper
powder is recovered by filtration, washed with water and then with
methanol and dried to obtain 149 g of activated copper powder.
[0494] It is easy to synthesize 4-perfluorohexylphenylboronic acid
by using the activated copper powder along the following path:
##STR00067##
[0495] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-perfluorohexylphenylboronic acid instead of the
4-methylphenylboronic acid in Example 11.
[0496]
Tetrakis[1-(4-perfluorohexylphenyl)isoquinoline-C.sup.2,N](.mu.-dic-
hloro)iridium (III) (Example Compound No. 715),
[0497]
Bis[1-(4-perfluorohexylphenyl)isoquinoline-C.sup.2,N]-(acetylaceton-
ato)iridium (III),
[0498]
Tris[1-(4-perfluorohexylphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 475).
Example 71
[0499] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-perfluorohexylphenylboronic acid and
1-chloro-4-fluoroisoquinoline instead of the 4-methylphenylboronic
acid and 1-chloroisoquinoline, respectively, in Example 11.
[0500]
Tetrakis[1-(4-perfluorohexylphenyl)-4-fluoroisoquinoline-C.sup.2,N]-
(.mu.-dichloro)diiridium (III).
[0501]
Bis[1-(4-perfluorohexylphenyl)-4-fluoroisoquinoline-C.sup.2,N](acet-
ylacetonato)iridium (III).
[0502]
Tris[1-(4-perfluorohexylphenyl)-4-fluoroisoquinoline-C.sup.2,N]irid-
ium (III) (Example Compound No. 478).
Example 72
[0503] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-perfluorohexylphenylboronic acid and
1-chloro-4-trifluoromethylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0504]
Tetrakis[1-(4-perfluorohexylphenyl)-4-trifluoromethylisoquinoline-C-
.sup.2,N](.mu.-dichloro)diiridium (III).
[0505]
Bis[1-(4-perfluorohexylphenyl)-4-trifluoromethylisoquinoline-C.sup.-
2,N](acetylacetonato)iridium (III).
[0506]
Tris[1-(4-perfluorohexylphenyl)-4-trifluoromethylisoquinoline-C.sup-
.2,N]iridium (III) (Example Compound No. 477).
Example 73
[0507] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-perfluorohexylphenylboronic acid and
1-chloro-5-fluoroisoquinoline instead of the 4-methylphenylboronic
acid and 1-chloroisoquinoline, respectively, in Example 11.
[0508]
Tetrakis[1-(4-perfluorohexylphenyl)-5-trifluoromethylisoquinoline-C-
.sup.2,N](.mu.-dichloro)diiridium (III).
[0509]
Bis[1-(4-perfluorohexylphenyl)-5-trifluoromethylisoquinoline-C.sup.-
2,N](acetylacetonato)iridium (III).
[0510]
Tris[1-(4-perfluorohexylphenyl)-5-trifluoromethylisoquinoline-C.sup-
.2,N]iridium (III) (Example Compound No. 476).
Example 74
[0511] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using
1-(4-perfluorohexylphenyl)isoquinoline instead of the
2-phenylpyridine in Example 22.
[0512]
Bis[1-(4-perfluorohexylphenyl)isoquinoline-C.sup.2,N](1-phenylisoqu-
inoline-C.sup.2,N)iridium (III) (Example Compound No. 479).
Example 75
[0513] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for, using 1-phenylisoquinoline and
1-(4-perfluorohexylphenyl)isoquinoline instead of the
2-phenylpyridine and 1-phenylisoquinoline, respectively, in Example
22.
[0514]
Bis(1-phenylisoquinoline-C.sup.2,N)[1-(4-perfluorohexylphenyl)isoqu-
inoline-C.sup.2,N]iridium (III) (Example Compound No. 480).
Example 76
[0515] It is easy to synthesize
4-(1H,1H,2H,2H-perfluoropentyloxy)phenylboronic acid along the
following the path:
##STR00068##
[0516] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-(1H,1H,2H,2H-perfluoropentyloxy)-phenylboronic acid instead of
the 4-methylphenylboronic acid in Example 11.
[0517]
Tetrakis{1-[4-(1H,1H,2H,2H-perfluoropentyloxy)phenyl]isoquinoline-C-
.sup.2,N}(.mu.-dichloro)iridium (III),
[0518]
Bis{1-[4-(1H,1H,2H,2H-perfluoropentyloxy)phenyl]-isoquinoline-C.sup-
.2,N}-(acetylacetonato)iridium (III),
[0519]
Tris{1-[4-(1H,1H,2H,2H-perfluoropentyloxyethylphenyl]isoquinoline-C-
.sup.2,N}-iridium (III) (Example Compound No. 469).
Example 77
[0520] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using
1-[4-(1H,1H,2H,2H-perfluoropentyloxy)isoquinoline instead of the
2-phenylpyridine in Example 22.
[0521]
Bis{1-[4-(1H,1H,2H,2H-perfluoropentyloxy)-phenyl]isoquinoline-C.sup-
.2,N}(1-phenylisoquinoline-C.sup.2,N)-iridium (III) (Example
Compound No. 470).
Example 78
[0522] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using 1-phenylisoquinoline and
1-[4-(1H,1H,2H,2H-perfluoropentyloxy)phenyl]isoquinoline instead of
the 2-phenylpyridine and 1-phenylisoquinoline, respectively, in
Example 22.
[0523]
Bis(1-phenylisoquinoline-C.sup.2,N){1-(4-(1H,1H,2H,2H-perfluoropent-
yloxy)phenyl]isoquinoline-C.sup.2,N}iridium (III) (Example Compound
No. 471).
Example 79
[0524] It is easy to synthesize
4-(1H,1H-perfluoroheptyloxy)phenylboronic acid along the following
path:
##STR00069##
[0525] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
4-(1H,1H-perfluoroheptyloxy)-phenylboronic acid instead of the
4-methylphenylboronic acid in Example 11.
[0526]
Tetrakis{1-[4-(1H,1H-perfluoroheptyloxy)phenyl]-isoquinoline-C.sup.-
2,N}(.mu.-dichloro)iridium (III),
[0527]
Bis{1-[4-(1H,1H-perfluoroheptyloxy)phenyl]-isoquinoline-C.sup.2,N}--
(acetylacetonato)iridium (III),
[0528]
Tris{1-[4-(1H,1H-perfluoroheptyloxy)phenyl]-isoquinoline-C.sup.2,N}-
-iridium (III) (Example Compound No. 481).
Example 80
[0529] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using
1-[4-(1H,1H-perfluoroheptyloxy)phenyl]-isoquinoline instead of the
2-phenylpyridine in Example 22.
[0530]
Bis{1-[4-(1H,1H-perfluoroheptyloxy)phenyl]-isoquinoline-C.sup.2,N}(-
1-phenylisoquinoline-C.sup.2,N)iridium (III) (Example Compound No.
483).
Example 81
[0531] It is easy to synthesize the following compound in a similar
manner as in Example 22 except for using 1-phenylisoquinoline and
1-[4-(1H,1H-perfluoroheptyloxy)phenyl]isoquinoline instead of the
2-phenylpyridine and 1-phenylisoquinoline, respectively, in Example
22.
[0532]
Bis(1-phenylisoquinoline-C.sup.2,N){1-[4-(1H,1H-perfluoroheptyloxy)-
phenyl]isoquinoline-C.sup.2,N}iridium (III) (Example Compound No.
484).
Example 82
[0533] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
phenylboronic acid and 1-chloro-4-hexylisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0534]
Tetrakis[1-phenyl-4-hexylisoquinoline-C.sup.2,N](.mu.-dichloro)diir-
idium (III).
[0535]
Bis[1-phenyl-4-hexylisoquinoline-C.sup.2,N](acetylacetonato)iridium
(III).
[0536] Tris[1-phenyl-4-hexylisoquinoline-C.sup.2,N]iridium (III)
(Example Compound No. 156).
Example 83
[0537] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
phenylboronic acid and 1-chloro-5-fluoroisoquinoline instead of the
4-methylphenylboronic acid and 1-chloroisoquinoline, respectively,
in Example 11.
[0538]
Tetrakis(1-phenyl-5-octylisoquinoline-C.sup.2,N)(.mu.-dichloro)diir-
idium (III).
[0539]
Bis(1-phenyl-5-octylisoquinoline-C.sup.2,N)(acetylacetonato)iridium
(III).
[0540] Tris(1-phenyl-5-octylisoquinoline-C.sup.2,N)iridium (III)
(Example Compound No. 220).
Example 84
[0541] It is easy to successively synthesize the following
compounds in the same manner as in Example 11 except for using
3-heptyloxyphenylboronic acid (made by Lancaster co.) instead of
the 4-methylphenylboronic acid in Example
[0542]
Tetrakis[1-(5-heptyloxyphenyl)isoquinoline-C.sup.2,N](.mu.-dichloro-
)iridium (III),
[0543]
Bis[1-(5-heptyloxyphenyl)isoquinoline-C.sup.2,N]-(acetylacetonato)i-
ridium (III),
[0544] Tris[1-(5-heptyloxyphenyl)isoquinoline-C.sup.2,N]-iridium
(III) (Example Compound No. 270).
Example 85
[0545] It is easy to synthesize 1-chloro-7-azaisoquinoline by using
2,6-dihydroxy-4-methyl-3-pyridylcarbonitrile (made by Aldrich Co.,
catalog 37, 947-6) along the following path described in U.S. Pat.
No. 4,859,671:
##STR00070##
[0546] It is easy to synthesize 1-phenyl-7-azaisoquinoline by using
1-chloro-7-azaisoquinoline instead of the 1-chloroisoquinoline in
Example 7, and successively synthesize
tetrakis(1-phenyl-7-azaisoquinoline-C.sup.2,N)(.mu.-dichloro)diiridium
(III) and
bis(1-phenyl-7-azaisoquinoline-C.sup.2,N)(acetylacetonato)-irid-
ium (III) to obtain
tris(1-phenyl-7-azaisoquinoline-C.sup.2,N)iridium (III) (Example
Compound No. 783) in a similar manner as in Example 11.
Example 66
[0547] It is easy to synthesize 1-hydroxy-5-azaisoquinoline by
using 3-methyl-picolinonitrile (made by Aldrich Co., catalog 51,
273-7) along the following path described in U.S. Pat. No.
4,176,183 and synthesize 1-chloro-5-azaisoquinoline in a similar
manner as in Example 85.
##STR00071##
[0548] It is easy to synthesize 1-phenyl-5-azaisoquinoline by using
1-chloro-5-azaisoquinoline instead of the 1-chloroisoquinoline in
Example 7, and successively synthesize
tetrakis(1-phenyl-5-azaisoquinoline-C.sup.2,N)(.mu.-dichloro)diiridium
(III) (Example Compound No. 763) and
bis(1-phenyl-5-azaisoquinoline-C.sup.2,N)(acetylacetonato)iridium
(III) to obtain tris(1-phenyl-5-azaisoquinoline-C.sup.2,N)iridium
(III) (Example Compound No. 640) in a similar Manner as in Example
11.
Examples 87-95
[0549] Devices having a similar structure as in Example 1 were
prepared and evaluated. Details, of device structures, layer
thicknesses and evaluation results are shown in Table 25.
TABLE-US-00040 TABLE 25 Device structure * Exam- luminescence
current luminance current efficiency power efficiency ple No.
H.T.L. layer E.D.P.L. E.T.L. mA/cm2 cd/m2 cd/A lm/W 87 .alpha.NPD
CBP: Compound BCP Alq 3 10 volts 10 volts 100 cd/m2 300 cd/m2 100
cd/m2 300 cd/m2 No. 413(7%) 40 nm 40 nm 10 nm 20 nm 114 800 1 0.86
0.4 0.3 88 .alpha.NPD CBP: Compound BCP Alq 3 10 V 10 V 100 cd 300
cd 100 cd 300 cd No. 432(7%) 40 40 10 20 26 1248 6.9 6.5 2.8 2.1 89
.alpha.NPD CBP: Compound BCP Alq 3 10 V 10 V 100 cd 300 cd 100 cd
300 cd No. 408(5%) 40 40 10 60 9 480 6.5 5.6 2.4 1.8 90 .alpha.NPD
CBP: Compound BCP Alq 3 10 V 10 V 100 cd 300 cd 100 cd 300 cd No.
433(5%) 40 40 10 60 12 700 6.69 6.4 2.93 2.32 91 .alpha.NPD CBP:
Compound BCP Alq 3 10 V 100 cd 300 cd 100 cd 300 cd No. 433(7%) 40
40 10 60 12.2 876 8.6 7.8 3.82 2.9 92 .alpha.NPD CBP: Compound BCP
Alq 3 10 V 100 cd 300 cd 100 cd 300 cd No. 433(9%) 40 40 10 60 18
1180 7.5 7.2 3.86 2.9 93 .alpha.NPD CBP: Compound BCP Alq 3 10 V
100 cd 300 cd 100 cd 300 cd No. 517(7%) 40 40 10 60 3.3 185 5.75
5.42 1.95 1.54 94 .alpha.NPD CBP: Compound Balq Alq 3 10 V 100 cd
300 cd 100 cd 300 cd No. 516(7%) 40 40 10 60 12.5 611 5.85 5.26
2.42 1.80 95 .alpha.NPD CBP: Compound Balq Alq 3 10 V 100 cd 100 cd
100 cd 300 cd No. 412(7%) 40 40 10 60 15 778 5.3 5.4 2.2 1.9 *
H.T.L. = hole-transporting layer E.D.P.L. = exciton
diffusion-prevention layer E.T.L. = electron-transporting layer
[0550] Balq used in the exciton diffusion-prevention layer used in
Examples 94 and 95 has a structure shown below.
##STR00072##
INDUSTRIAL APPLICABILITY
[0551] As described above, the luminescence device of the present
invention using, as a luminescence center material, a metal
coordination compound having a partial structure of the above
formula (1) and particularly represented by the above formula (3)
is an excellent device which not only allows high-efficiency
luminescence but also retains a high luminance for a long period
and allows luminescence of longer wavelength. Further, the
luminescence device of the present invention shows excellent
performances as a red display device.
* * * * *